Revert cosign (see #7536 )

build(deps): bump the actions-deps group across 1 directory with 12 updates (#7536 )
Bumps the actions-deps group with 12 updates in the / directory: | Package | From | To | | --- | --- | --- | | [actions/checkout](https://github.com/actions/checkout) | `5.0.0` | `6.0.2` | | [github/ai-moderator](https://github.com/github/ai-moderator) | `1.1.2` | `1.1.4` | | [step-security/harden-runner](https://github.com/step-security/harden-runner) | `2.13.1` | `2.15.0` | | [actions/setup-go](https://github.com/actions/setup-go) | `6.0.0` | `6.3.0` | | [actions/upload-artifact](https://github.com/actions/upload-artifact) | `4.6.2` | `7.0.0` | | [goreleaser/goreleaser-action](https://github.com/goreleaser/goreleaser-action) | `6.4.0` | `7.0.0` | | [golangci/golangci-lint-action](https://github.com/golangci/golangci-lint-action) | `8.0.0` | `9.2.0` | | [actions/dependency-review-action](https://github.com/actions/dependency-review-action) | `4.8.0` | `4.8.3` | | [sigstore/cosign-installer](https://github.com/sigstore/cosign-installer) | `3.10.0` | `4.0.0` | | [anchore/sbom-action](https://github.com/anchore/sbom-action) | `0.20.6` | `0.23.0` | | [peter-evans/repository-dispatch](https://github.com/peter-evans/repository-dispatch) | `4.0.0` | `4.0.1` | | [github/codeql-action](https://github.com/github/codeql-action) | `3.30.5` | `4.32.4` | Updates `actions/checkout` from 5.0.0 to 6.0.2 - [Release notes](https://github.com/actions/checkout/releases) - [Changelog](https://github.com/actions/checkout/blob/main/CHANGELOG.md) - [Commits](https://github.com/actions/checkout/compare/08c6903cd8c0fde910a37f88322edcfb5dd907a8...de0fac2e4500dabe0009e67214ff5f5447ce83dd) Updates `github/ai-moderator` from 1.1.2 to 1.1.4 - [Release notes](https://github.com/github/ai-moderator/releases) - [Commits](https://github.com/github/ai-moderator/compare/6bcdb2a79c2e564db8d76d7d4439d91a044c4eb6...81159c370785e295c97461ade67d7c33576e9319) Updates `step-security/harden-runner` from 2.13.1 to 2.15.0 - [Release notes](https://github.com/step-security/harden-runner/releases) - [Commits](https://github.com/step-security/harden-runner/compare/f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a...a90bcbc6539c36a85cdfeb73f7e2f433735f215b) Updates `actions/setup-go` from 6.0.0 to 6.3.0 - [Release notes](https://github.com/actions/setup-go/releases) - [Commits](https://github.com/actions/setup-go/compare/44694675825211faa026b3c33043df3e48a5fa00...4b73464bb391d4059bd26b0524d20df3927bd417) Updates `actions/upload-artifact` from 4.6.2 to 7.0.0 - [Release notes](https://github.com/actions/upload-artifact/releases) - [Commits](https://github.com/actions/upload-artifact/compare/ea165f8d65b6e75b540449e92b4886f43607fa02...bbbca2ddaa5d8feaa63e36b76fdaad77386f024f) Updates `goreleaser/goreleaser-action` from 6.4.0 to 7.0.0 - [Release notes](https://github.com/goreleaser/goreleaser-action/releases) - [Commits](https://github.com/goreleaser/goreleaser-action/compare/e435ccd777264be153ace6237001ef4d979d3a7a...ec59f474b9834571250b370d4735c50f8e2d1e29) Updates `golangci/golangci-lint-action` from 8.0.0 to 9.2.0 - [Release notes](https://github.com/golangci/golangci-lint-action/releases) - [Commits](https://github.com/golangci/golangci-lint-action/compare/4afd733a84b1f43292c63897423277bb7f4313a9...1e7e51e771db61008b38414a730f564565cf7c20) Updates `actions/dependency-review-action` from 4.8.0 to 4.8.3 - [Release notes](https://github.com/actions/dependency-review-action/releases) - [Commits](https://github.com/actions/dependency-review-action/compare/56339e523c0409420f6c2c9a2f4292bbb3c07dd3...05fe4576374b728f0c523d6a13d64c25081e0803) Updates `sigstore/cosign-installer` from 3.10.0 to 4.0.0 - [Release notes](https://github.com/sigstore/cosign-installer/releases) - [Commits](https://github.com/sigstore/cosign-installer/compare/d7543c93d881b35a8faa02e8e3605f69b7a1ce62...faadad0cce49287aee09b3a48701e75088a2c6ad) Updates `anchore/sbom-action` from 0.20.6 to 0.23.0 - [Release notes](https://github.com/anchore/sbom-action/releases) - [Changelog](https://github.com/anchore/sbom-action/blob/main/RELEASE.md) - [Commits](https://github.com/anchore/sbom-action/compare/f8bdd1d8ac5e901a77a92f111440fdb1b593736b...17ae1740179002c89186b61233e0f892c3118b11) Updates `peter-evans/repository-dispatch` from 4.0.0 to 4.0.1 - [Release notes](https://github.com/peter-evans/repository-dispatch/releases) - [Commits](https://github.com/peter-evans/repository-dispatch/compare/5fc4efd1a4797ddb68ffd0714a238564e4cc0e6f...28959ce8df70de7be546dd1250a005dd32156697) Updates `github/codeql-action` from 3.30.5 to 4.32.4 - [Release notes](https://github.com/github/codeql-action/releases) - [Changelog](https://github.com/github/codeql-action/blob/main/CHANGELOG.md) - [Commits](https://github.com/github/codeql-action/compare/3599b3baa15b485a2e49ef411a7a4bb2452e7f93...89a39a4e59826350b863aa6b6252a07ad50cf83e) --- updated-dependencies: - dependency-name: actions/checkout dependency-version: 6.0.2 dependency-type: direct:production update-type: version-update:semver-major dependency-group: actions-deps - dependency-name: github/ai-moderator dependency-version: 1.1.4 dependency-type: direct:production update-type: version-update:semver-patch dependency-group: actions-deps - dependency-name: step-security/harden-runner dependency-version: 2.15.0 dependency-type: direct:production update-type: version-update:semver-minor dependency-group: actions-deps - dependency-name: actions/setup-go dependency-version: 6.3.0 dependency-type: direct:production update-type: version-update:semver-minor dependency-group: actions-deps - dependency-name: actions/upload-artifact dependency-version: 7.0.0 dependency-type: direct:production update-type: version-update:semver-major dependency-group: actions-deps - dependency-name: goreleaser/goreleaser-action dependency-version: 7.0.0 dependency-type: direct:production update-type: version-update:semver-major dependency-group: actions-deps - dependency-name: golangci/golangci-lint-action dependency-version: 9.2.0 dependency-type: direct:production update-type: version-update:semver-major dependency-group: actions-deps - dependency-name: actions/dependency-review-action dependency-version: 4.8.3 dependency-type: direct:production update-type: version-update:semver-patch dependency-group: actions-deps - dependency-name: sigstore/cosign-installer dependency-version: 4.0.0 dependency-type: direct:production update-type: version-update:semver-major dependency-group: actions-deps - dependency-name: anchore/sbom-action dependency-version: 0.23.0 dependency-type: direct:production update-type: version-update:semver-minor dependency-group: actions-deps - dependency-name: peter-evans/repository-dispatch dependency-version: 4.0.1 dependency-type: direct:production update-type: version-update:semver-patch dependency-group: actions-deps - dependency-name: github/codeql-action dependency-version: 4.32.4 dependency-type: direct:production update-type: version-update:semver-major dependency-group: actions-deps ... Signed-off-by: dependabot[bot] <support@github.com> Co-authored-by: dependabot[bot] <49699333+dependabot[bot]@users.noreply.github.com>
2026-05-26 08:42:31 -04:00 · 2026-03-05 08:41:54 -07:00 · 2026-03-04 21:29:44 -07:00 · 2026-03-04 21:26:18 -07:00 · 2026-03-04 17:14:52 -07:00 · 2026-03-04 16:18:33 -07:00
83 changed files with 4628 additions and 684 deletions
@@ -1,15 +1,14 @@
 # Security Policy

-The Caddy project would like to make sure that it stays on top of all practically-exploitable vulnerabilities.
+The Caddy project would like to make sure that it stays on top of all relevant and practically-exploitable vulnerabilities.


 ## Supported Versions

-| Version  | Supported |
-| -------- | ----------|
-| 2.latest | ✔️        |
-| 1.x      | :x:       |
-| < 1.x    | :x:       |
+| Version     | Supported |
+| ----------- | ----------|
+| 2.latest    | ✔️        |
+| <= 2.latest | :x:       |


 ## Acceptable Scope
@@ -26,6 +25,8 @@ Client-side exploits are out of scope. In other words, it is not a bug in Caddy

 Security bugs in code dependencies (including Go's standard library) are out of scope. Instead, if a dependency has patched a relevant security bug, please feel free to open a public issue or pull request to update that dependency in our code.

+We accept security reports and patches, but do not assign CVEs, for code that has not been released with a non-prerelease tag.
+

 ## Reporting a Vulnerability

@@ -33,7 +34,7 @@ We get a lot of difficult reports that turn out to be invalid. Clear, obvious re

 First please ensure your report falls within the accepted scope of security bugs (above).

-**YOU MUST DISCLOSE THE USE OF LLMs ("AI") INVOLVED IN ANY WAY.** Whether you are using AI for discovery, as part of writing the report or its replies, and/or testing or validating proofs and changes, we require you to mention the extent of it. **FAILURE TO INCLUDE A DISCLOSURE MAY LEAD TO IMMEDIATE DISMISSAL OF YOUR REPORT AND POTENTIAL BLOCKLISTING.**
+:warning: **YOU MUST DISCLOSE WHETHER YOU USED LLMs ("AI") IN ANY WAY.** Whether you are using AI for discovery, as part of writing the report or its replies, and/or testing or validating proofs and changes, we require you to mention the extent of it. **FAILURE TO INCLUDE A DISCLOSURE EVEN IF YOU DO NOT USE AI MAY LEAD TO IMMEDIATE DISMISSAL OF YOUR REPORT AND POTENTIAL BLOCKLISTING.** We will not waste our time chatting with bots. But if you're a human, pull up a chair and we'll drink some chocolate milk.

 We'll need enough information to verify the bug and make a patch. To speed things up, please include:

@@ -16,8 +16,8 @@ jobs:
      models: read
      contents: read
    steps:
-      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8
-      - uses: github/ai-moderator@6bcdb2a79c2e564db8d76d7d4439d91a044c4eb6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd
+      - uses: github/ai-moderator@81159c370785e295c97461ade67d7c33576e9319
        with:
          token: ${{ secrets.GITHUB_TOKEN }}
          spam-label: 'spam'
@@ -65,15 +65,15 @@ jobs:
      actions: write # to allow uploading artifacts and cache
    steps:
    - name: Harden the runner (Audit all outbound calls)
-      uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+      uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
      with:
        egress-policy: audit

    - name: Checkout code
-      uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+      uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2

    - name: Install Go
-      uses: actions/setup-go@44694675825211faa026b3c33043df3e48a5fa00 # v6.0.0
+      uses: actions/setup-go@4b73464bb391d4059bd26b0524d20df3927bd417 # v6.3.0
      with:
        go-version: ${{ matrix.GO_SEMVER }}
        check-latest: true
@@ -120,7 +120,7 @@ jobs:
        ./caddy stop

    - name: Publish Build Artifact
-      uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+      uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
      with:
        name: caddy_${{ runner.os }}_go${{ matrix.go }}_${{ steps.vars.outputs.short_sha }}
        path: ${{ matrix.CADDY_BIN_PATH }}
@@ -162,13 +162,13 @@ jobs:
    continue-on-error: true  # August 2020: s390x VM is down due to weather and power issues
    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit
          allowed-endpoints: ci-s390x.caddyserver.com:22

      - name: Checkout code
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
      - name: Run Tests
        run: |
          set +e
@@ -221,19 +221,19 @@ jobs:
    if: github.event.pull_request.head.repo.full_name == 'caddyserver/caddy' && github.actor != 'dependabot[bot]'
    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit

      - name: Checkout code
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
      
-      - uses: goreleaser/goreleaser-action@e435ccd777264be153ace6237001ef4d979d3a7a # v6.4.0
+      - uses: goreleaser/goreleaser-action@ec59f474b9834571250b370d4735c50f8e2d1e29 # v7.0.0
        with:
          version: latest
          args: check
      - name: Install Go
-        uses: actions/setup-go@44694675825211faa026b3c33043df3e48a5fa00 # v6.0.0
+        uses: actions/setup-go@4b73464bb391d4059bd26b0524d20df3927bd417 # v6.3.0
        with:
          go-version: "~1.26"
          check-latest: true
@@ -241,7 +241,7 @@ jobs:
        run: |
          go install github.com/caddyserver/xcaddy/cmd/xcaddy@latest
          xcaddy version
-      - uses: goreleaser/goreleaser-action@e435ccd777264be153ace6237001ef4d979d3a7a # v6.4.0
+      - uses: goreleaser/goreleaser-action@ec59f474b9834571250b370d4735c50f8e2d1e29 # v7.0.0
        with:
          version: latest
          args: build --single-target --snapshot
@@ -51,15 +51,15 @@ jobs:
    continue-on-error: true
    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit

      - name: Checkout code
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2

      - name: Install Go
-        uses: actions/setup-go@44694675825211faa026b3c33043df3e48a5fa00 # v6.0.0
+        uses: actions/setup-go@4b73464bb391d4059bd26b0524d20df3927bd417 # v6.3.0
        with:
          go-version: ${{ matrix.GO_SEMVER }}
          check-latest: true
@@ -45,18 +45,18 @@ jobs:

    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit

-      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
-      - uses: actions/setup-go@44694675825211faa026b3c33043df3e48a5fa00 # v6.0.0
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-go@4b73464bb391d4059bd26b0524d20df3927bd417 # v6.3.0
        with:
          go-version: '~1.26'
          check-latest: true

      - name: golangci-lint
-        uses: golangci/golangci-lint-action@4afd733a84b1f43292c63897423277bb7f4313a9 # v8.0.0
+        uses: golangci/golangci-lint-action@1e7e51e771db61008b38414a730f564565cf7c20 # v9.2.0
        with:
          version: latest

@@ -73,7 +73,7 @@ jobs:
    runs-on: ubuntu-latest
    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit

@@ -90,14 +90,14 @@ jobs:
      pull-requests: write
    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit

      - name: 'Checkout Repository'
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
      - name: 'Dependency Review'
-        uses: actions/dependency-review-action@56339e523c0409420f6c2c9a2f4292bbb3c07dd3 # v4.8.0
+        uses: actions/dependency-review-action@05fe4576374b728f0c523d6a13d64c25081e0803 # v4.8.3
        with:
          comment-summary-in-pr: on-failure
          # https://github.com/actions/dependency-review-action/issues/430#issuecomment-1468975566
@@ -28,11 +28,11 @@ jobs:
    
    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit
      - name: Checkout code
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0

@@ -28,7 +28,7 @@ jobs:
    
    steps:
      - name: Checkout code
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          fetch-depth: 0
      # Force fetch upstream tags -- because 65 minutes
@@ -355,23 +355,23 @@ jobs:

    steps:
    - name: Harden the runner (Audit all outbound calls)
-      uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+      uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
      with:
        egress-policy: audit

    - name: Checkout code
-      uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+      uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
      with:
        fetch-depth: 0

    - name: Install Go
-      uses: actions/setup-go@44694675825211faa026b3c33043df3e48a5fa00 # v6.0.0
+      uses: actions/setup-go@4b73464bb391d4059bd26b0524d20df3927bd417 # v6.3.0
      with:
        go-version: ${{ matrix.GO_SEMVER }}
        check-latest: true

    # Force fetch upstream tags -- because 65 minutes
-    # tl;dr: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v4.2.2 runs this line:
+    # tl;dr: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v4.2.2 runs this line:
    #   git -c protocol.version=2 fetch --no-tags --prune --progress --no-recurse-submodules --depth=1 origin +ebc278ec98bb24f2852b61fde2a9bf2e3d83818b:refs/tags/
    # which makes its own local lightweight tag, losing all the annotations in the process. Our earlier script ran:
    #   git fetch --prune --unshallow
@@ -419,7 +419,7 @@ jobs:
    - name: Cosign version
      run: cosign version
    - name: Install Syft
-      uses: anchore/sbom-action/download-syft@f8bdd1d8ac5e901a77a92f111440fdb1b593736b # main
+      uses: anchore/sbom-action/download-syft@17ae1740179002c89186b61233e0f892c3118b11 # main
    - name: Syft version
      run: syft version
    - name: Install xcaddy
@@ -428,7 +428,7 @@ jobs:
        xcaddy version
    # GoReleaser will take care of publishing those artifacts into the release
    - name: Run GoReleaser
-      uses: goreleaser/goreleaser-action@e435ccd777264be153ace6237001ef4d979d3a7a # v6.4.0
+      uses: goreleaser/goreleaser-action@ec59f474b9834571250b370d4735c50f8e2d1e29 # v7.0.0
      with:
        version: latest
        args: release --clean --timeout 60m
@@ -24,12 +24,12 @@ jobs:

    # See https://github.com/peter-evans/repository-dispatch
    - name: Harden the runner (Audit all outbound calls)
-      uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+      uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
      with:
        egress-policy: audit

    - name: Trigger event on caddyserver/dist
-      uses: peter-evans/repository-dispatch@5fc4efd1a4797ddb68ffd0714a238564e4cc0e6f # v4.0.0
+      uses: peter-evans/repository-dispatch@28959ce8df70de7be546dd1250a005dd32156697 # v4.0.1
      with:
        token: ${{ secrets.REPO_DISPATCH_TOKEN }}
        repository: caddyserver/dist
@@ -37,7 +37,7 @@ jobs:
        client-payload: '{"tag": "${{ github.event.release.tag_name }}"}'

    - name: Trigger event on caddyserver/caddy-docker
-      uses: peter-evans/repository-dispatch@5fc4efd1a4797ddb68ffd0714a238564e4cc0e6f # v4.0.0
+      uses: peter-evans/repository-dispatch@28959ce8df70de7be546dd1250a005dd32156697 # v4.0.1
      with:
        token: ${{ secrets.REPO_DISPATCH_TOKEN }}
        repository: caddyserver/caddy-docker
@@ -37,12 +37,12 @@ jobs:

    steps:
      - name: Harden the runner (Audit all outbound calls)
-        uses: step-security/harden-runner@f4a75cfd619ee5ce8d5b864b0d183aff3c69b55a # v2.13.1
+        uses: step-security/harden-runner@a90bcbc6539c36a85cdfeb73f7e2f433735f215b # v2.15.0
        with:
          egress-policy: audit

      - name: "Checkout code"
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
        with:
          persist-credentials: false

@@ -72,7 +72,7 @@ jobs:
      # Upload the results as artifacts (optional). Commenting out will disable uploads of run results in SARIF
      # format to the repository Actions tab.
      - name: "Upload artifact"
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7.0.0
        with:
          name: SARIF file
          path: results.sarif
@@ -81,6 +81,6 @@ jobs:
      # Upload the results to GitHub's code scanning dashboard (optional).
      # Commenting out will disable upload of results to your repo's Code Scanning dashboard
      - name: "Upload to code-scanning"
-        uses: github/codeql-action/upload-sarif@3599b3baa15b485a2e49ef411a7a4bb2452e7f93 # v3.29.5
+        uses: github/codeql-action/upload-sarif@89a39a4e59826350b863aa6b6252a07ad50cf83e # v3.29.5
        with:
          sarif_file: results.sarif
@@ -32,6 +32,7 @@ linters:
    - importas
    - ineffassign
    - misspell
+    - modernize
    - prealloc
    - promlinter
    - sloglint
@@ -13,7 +13,7 @@ before:
    - cp cmd/caddy/main.go caddy-build/main.go
    - /bin/sh -c 'cd ./caddy-build && go mod init caddy'
    # prepare syso files for windows embedding
-    - /bin/sh -c 'for a in amd64 arm arm64; do XCADDY_SKIP_BUILD=1 GOOS=windows GOARCH=$a xcaddy build {{.Env.TAG}}; done'
+    - /bin/sh -c 'for a in amd64 arm64; do XCADDY_SKIP_BUILD=1 GOOS=windows GOARCH=$a xcaddy build {{.Env.TAG}}; done'
    - /bin/sh -c 'mv /tmp/buildenv_*/*.syso caddy-build'
    # GoReleaser doesn't seem to offer {{.Tag}} at this stage, so we have to embed it into the env
    # so we run: TAG=$(git describe --abbrev=0) goreleaser release --rm-dist --skip-publish --skip-validate
@@ -67,6 +67,8 @@ builds:
      goarch: s390x
    - goos: windows
      goarch: riscv64
+    - goos: windows
+      goarch: arm
    - goos: freebsd
      goarch: ppc64le
    - goos: freebsd
@@ -749,10 +749,14 @@ func stopAdminServer(srv *http.Server) error {
 	if srv == nil {
 		return fmt.Errorf("no admin server")
 	}
-	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+	timeout := 10 * time.Second
+	ctx, cancel := context.WithTimeoutCause(context.Background(), timeout, fmt.Errorf("stopping admin server: %ds timeout", int(timeout.Seconds())))
 	defer cancel()
 	err := srv.Shutdown(ctx)
 	if err != nil {
+		if cause := context.Cause(ctx); cause != nil && errors.Is(err, context.DeadlineExceeded) {
+			err = cause
+		}
 		return fmt.Errorf("shutting down admin server: %v", err)
 	}
 	Log().Named("admin").Info("stopped previous server", zap.String("address", srv.Addr))
@@ -88,7 +88,7 @@ type Config struct {
 	storage      certmagic.Storage
 	eventEmitter eventEmitter

-	cancelFunc context.CancelFunc
+	cancelFunc context.CancelCauseFunc

 	// fileSystems is a dict of fileSystems that will later be loaded from and added to.
 	fileSystems FileSystems
@@ -227,8 +227,18 @@ func changeConfig(method, path string, input []byte, ifMatchHeader string, force
 	idx := make(map[string]string)
 	err = indexConfigObjects(rawCfg[rawConfigKey], "/"+rawConfigKey, idx)
 	if err != nil {
+		if len(rawCfgJSON) > 0 {
+			var oldCfg any
+			err2 := json.Unmarshal(rawCfgJSON, &oldCfg)
+			if err2 != nil {
+				err = fmt.Errorf("%v; additionally, restoring old config: %v", err, err2)
+			}
+			rawCfg[rawConfigKey] = oldCfg
+		} else {
+			rawCfg[rawConfigKey] = nil
+		}
 		return APIError{
-			HTTPStatus: http.StatusInternalServerError,
+			HTTPStatus: http.StatusBadRequest,
 			Err:        fmt.Errorf("indexing config: %v", err),
 		}
 	}
@@ -248,6 +258,8 @@ func changeConfig(method, path string, input []byte, ifMatchHeader string, force
 				err = fmt.Errorf("%v; additionally, restoring old config: %v", err, err2)
 			}
 			rawCfg[rawConfigKey] = oldCfg
+		} else {
+			rawCfg[rawConfigKey] = nil
 		}

 		return fmt.Errorf("loading new config: %v", err)
@@ -281,14 +293,19 @@ func indexConfigObjects(ptr any, configPath string, index map[string]string) err
 	case map[string]any:
 		for k, v := range val {
 			if k == idKey {
+				var idStr string
 				switch idVal := v.(type) {
 				case string:
-					index[idVal] = configPath
+					idStr = idVal
 				case float64: // all JSON numbers decode as float64
-					index[fmt.Sprintf("%v", idVal)] = configPath
+					idStr = fmt.Sprintf("%v", idVal)
 				default:
 					return fmt.Errorf("%s: %s field must be a string or number", configPath, idKey)
 				}
+				if existingPath, ok := index[idStr]; ok {
+					return fmt.Errorf("duplicate ID '%s' found at %s and %s", idStr, existingPath, configPath)
+				}
+				index[idStr] = configPath
 				continue
 			}
 			// traverse this object property recursively
@@ -416,7 +433,7 @@ func run(newCfg *Config, start bool) (Context, error) {
 		// partially copied from provisionContext
 		if err != nil {
 			globalMetrics.configSuccess.Set(0)
-			ctx.cfg.cancelFunc()
+			ctx.cfg.cancelFunc(fmt.Errorf("configuration start error: %w", err))

 			if currentCtx.cfg != nil {
 				certmagic.Default.Storage = currentCtx.cfg.storage
@@ -492,7 +509,7 @@ func provisionContext(newCfg *Config, replaceAdminServer bool) (Context, error)
 	// cleanup occurs when we return if there
 	// was an error; if no error, it will get
 	// cleaned up on next config cycle
-	ctx, cancel := NewContext(Context{Context: context.Background(), cfg: newCfg})
+	ctx, cancelCause := NewContextWithCause(Context{Context: context.Background(), cfg: newCfg})
 	defer func() {
 		if err != nil {
 			globalMetrics.configSuccess.Set(0)
@@ -501,7 +518,7 @@ func provisionContext(newCfg *Config, replaceAdminServer bool) (Context, error)
 			// since the associated config won't be used;
 			// this will cause all modules that were newly
 			// provisioned to clean themselves up
-			cancel()
+			cancelCause(fmt.Errorf("configuration error: %w", err))

 			// also undo any other state changes we made
 			if currentCtx.cfg != nil {
@@ -509,7 +526,7 @@ func provisionContext(newCfg *Config, replaceAdminServer bool) (Context, error)
 			}
 		}
 	}()
-	newCfg.cancelFunc = cancel // clean up later
+	newCfg.cancelFunc = cancelCause // clean up later

 	// set up logging before anything bad happens
 	if newCfg.Logging == nil {
@@ -729,7 +746,7 @@ func unsyncedStop(ctx Context) {
 	}

 	// clean up all modules
-	ctx.cfg.cancelFunc()
+	ctx.cfg.cancelFunc(fmt.Errorf("stopping apps"))
 }

 // Validate loads, provisions, and validates
@@ -737,7 +754,7 @@ func unsyncedStop(ctx Context) {
 func Validate(cfg *Config) error {
 	_, err := run(cfg, false)
 	if err == nil {
-		cfg.cancelFunc() // call Cleanup on all modules
+		cfg.cancelFunc(fmt.Errorf("validation complete")) // call Cleanup on all modules
 	}
 	return err
 }
@@ -945,6 +962,34 @@ func InstanceID() (uuid.UUID, error) {
 // for example.
 var CustomVersion string

+// CustomBinaryName is an optional string that overrides the root
+// command name from the default of "caddy". This is useful for
+// downstream projects that embed Caddy but use a different binary
+// name. Shell completions and help text will use this name instead
+// of "caddy".
+//
+// Set this variable during `go build` with `-ldflags`:
+//
+//	-ldflags '-X github.com/caddyserver/caddy/v2.CustomBinaryName=my_custom_caddy'
+//
+// for example.
+var CustomBinaryName string
+
+// CustomLongDescription is an optional string that overrides the
+// long description of the root Cobra command. This is useful for
+// downstream projects that embed Caddy but want different help
+// output.
+//
+// Set this variable in an init() function of a package that is
+// imported by your main:
+//
+//	func init() {
+//	    caddy.CustomLongDescription = "My custom server based on Caddy..."
+//	}
+//
+// for example.
+var CustomLongDescription string
+
 // Version returns the Caddy version in a simple/short form, and
 // a full version string. The short form will not have spaces and
 // is intended for User-Agent strings and similar, but may be
@@ -270,7 +270,7 @@ func (d *Dispenser) File() string {
 // targets are left unchanged. If all the targets are filled,
 // then true is returned.
 func (d *Dispenser) Args(targets ...*string) bool {
-	for i := 0; i < len(targets); i++ {
+	for i := range targets {
 		if !d.NextArg() {
 			return false
 		}
@@ -507,7 +507,7 @@ func (p *parser) doImport(nesting int) error {
 		// format, won't check for nesting correctness or any other error, that's what parser does.
 		if !maybeSnippet && nesting == 0 {
 			// first of the line
-			if i == 0 || isNextOnNewLine(tokensCopy[i-1], token) {
+			if i == 0 || isNextOnNewLine(tokensCopy[len(tokensCopy)-1], token) {
 				index = 0
 			} else {
 				index++
@@ -616,7 +616,7 @@ func (p *parser) doSingleImport(importFile string) ([]Token, error) {
 	if err != nil {
 		return nil, p.Errf("Failed to get absolute path of file: %s: %v", importFile, err)
 	}
-	for i := 0; i < len(importedTokens); i++ {
+	for i := range importedTokens {
 		importedTokens[i].File = filename
 	}

@@ -822,7 +822,7 @@ func (st *ServerType) serversFromPairings(
 				// https://caddy.community/t/making-sense-of-auto-https-and-why-disabling-it-still-serves-https-instead-of-http/9761
 				createdTLSConnPolicies, ok := sblock.pile["tls.connection_policy"]
 				hasTLSEnabled := (ok && len(createdTLSConnPolicies) > 0) ||
-					(addr.Host != "" && srv.AutoHTTPS != nil && !slices.Contains(srv.AutoHTTPS.Skip, addr.Host))
+					(addr.Host != "" && (srv.AutoHTTPS == nil || !slices.Contains(srv.AutoHTTPS.Skip, addr.Host)))

 				// we'll need to remember if the address qualifies for auto-HTTPS, so we
 				// can add a TLS conn policy if necessary
@@ -1,9 +1,11 @@
 package httpcaddyfile

 import (
+	"encoding/json"
 	"testing"

 	"github.com/caddyserver/caddy/v2/caddyconfig/caddyfile"
+	"github.com/caddyserver/caddy/v2/modules/caddyhttp"
 )

 func TestMatcherSyntax(t *testing.T) {
@@ -209,3 +211,53 @@ func TestGlobalOptions(t *testing.T) {
 		}
 	}
 }
+
+func TestDefaultSNIWithoutHTTPS(t *testing.T) {
+	caddyfileStr := `{
+		default_sni my-sni.com
+	}
+	example.com {
+	}`
+
+	adapter := caddyfile.Adapter{
+		ServerType: ServerType{},
+	}
+
+	result, _, err := adapter.Adapt([]byte(caddyfileStr), nil)
+	if err != nil {
+		t.Fatalf("Failed to adapt Caddyfile: %v", err)
+	}
+
+	var config struct {
+		Apps struct {
+			HTTP struct {
+				Servers map[string]*caddyhttp.Server `json:"servers"`
+			} `json:"http"`
+		} `json:"apps"`
+	}
+
+	if err := json.Unmarshal(result, &config); err != nil {
+		t.Fatalf("Failed to unmarshal JSON config: %v", err)
+	}
+
+	server, ok := config.Apps.HTTP.Servers["srv0"]
+	if !ok {
+		t.Fatalf("Expected server 'srv0' to be created")
+	}
+
+	if len(server.TLSConnPolicies) == 0 {
+		t.Fatalf("Expected TLS connection policies to be generated, got none")
+	}
+
+	found := false
+	for _, policy := range server.TLSConnPolicies {
+		if policy.DefaultSNI == "my-sni.com" {
+			found = true
+			break
+		}
+	}
+
+	if !found {
+		t.Errorf("Expected default_sni 'my-sni.com' in TLS connection policies, but it was missing. Generated JSON: %s", string(result))
+	}
+}
@@ -64,6 +64,7 @@ func init() {
 	RegisterGlobalOption("preferred_chains", parseOptPreferredChains)
 	RegisterGlobalOption("persist_config", parseOptPersistConfig)
 	RegisterGlobalOption("dns", parseOptDNS)
+	RegisterGlobalOption("tls_resolvers", parseOptTLSResolvers)
 	RegisterGlobalOption("ech", parseOptECH)
 	RegisterGlobalOption("renewal_window_ratio", parseOptRenewalWindowRatio)
 }
@@ -306,6 +307,15 @@ func parseOptSingleString(d *caddyfile.Dispenser, _ any) (any, error) {
 	return val, nil
 }

+func parseOptTLSResolvers(d *caddyfile.Dispenser, _ any) (any, error) {
+	d.Next() // consume option name
+	resolvers := d.RemainingArgs()
+	if len(resolvers) == 0 {
+		return nil, d.ArgErr()
+	}
+	return resolvers, nil
+}
+
 func parseOptDefaultBind(d *caddyfile.Dispenser, _ any) (any, error) {
 	d.Next() // consume option name

@@ -1,9 +1,11 @@
 package httpcaddyfile

 import (
+	"encoding/json"
 	"testing"

 	"github.com/caddyserver/caddy/v2/caddyconfig/caddyfile"
+	"github.com/caddyserver/caddy/v2/modules/caddytls"
 	_ "github.com/caddyserver/caddy/v2/modules/logging"
 )

@@ -62,3 +64,105 @@ func TestGlobalLogOptionSyntax(t *testing.T) {
 		}
 	}
 }
+
+func TestGlobalResolversOption(t *testing.T) {
+	tests := []struct {
+		name            string
+		input           string
+		expectResolvers []string
+		expectError     bool
+	}{
+		{
+			name: "single resolver",
+			input: `{
+				tls_resolvers 1.1.1.1
+			}
+			example.com {
+			}`,
+			expectResolvers: []string{"1.1.1.1"},
+			expectError:     false,
+		},
+		{
+			name: "two resolvers",
+			input: `{
+				tls_resolvers 1.1.1.1 8.8.8.8
+			}
+			example.com {
+			}`,
+			expectResolvers: []string{"1.1.1.1", "8.8.8.8"},
+			expectError:     false,
+		},
+		{
+			name: "multiple resolvers",
+			input: `{
+				tls_resolvers 1.1.1.1 8.8.8.8 9.9.9.9
+			}
+			example.com {
+			}`,
+			expectResolvers: []string{"1.1.1.1", "8.8.8.8", "9.9.9.9"},
+			expectError:     false,
+		},
+		{
+			name: "no resolvers specified",
+			input: `{
+			}
+			example.com {
+			}`,
+			expectResolvers: nil,
+			expectError:     false,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			adapter := caddyfile.Adapter{
+				ServerType: ServerType{},
+			}
+
+			out, _, err := adapter.Adapt([]byte(tc.input), nil)
+
+			if (err != nil) != tc.expectError {
+				t.Errorf("error expectation failed. Expected error: %v, got: %v", tc.expectError, err)
+				return
+			}
+
+			if tc.expectError {
+				return
+			}
+
+			// Parse the output JSON to check resolvers
+			var config struct {
+				Apps struct {
+					TLS *caddytls.TLS `json:"tls"`
+				} `json:"apps"`
+			}
+
+			if err := json.Unmarshal(out, &config); err != nil {
+				t.Errorf("failed to unmarshal output: %v", err)
+				return
+			}
+
+			// Check if resolvers match expected
+			if config.Apps.TLS == nil {
+				if tc.expectResolvers != nil {
+					t.Errorf("Expected TLS config with resolvers %v, but TLS config is nil", tc.expectResolvers)
+				}
+				return
+			}
+
+			actualResolvers := config.Apps.TLS.Resolvers
+			if len(tc.expectResolvers) == 0 && len(actualResolvers) == 0 {
+				return // Both empty, ok
+			}
+			if len(actualResolvers) != len(tc.expectResolvers) {
+				t.Errorf("Expected %d resolvers, got %d. Expected: %v, got: %v", len(tc.expectResolvers), len(actualResolvers), tc.expectResolvers, actualResolvers)
+				return
+			}
+			for j, expected := range tc.expectResolvers {
+				if actualResolvers[j] != expected {
+					t.Errorf("Resolver %d mismatch. Expected: %s, got: %s", j, expected, actualResolvers[j])
+				}
+			}
+		})
+	}
+}
@@ -334,6 +334,11 @@ func (st ServerType) buildTLSApp(
 		tlsApp.DNSRaw = caddyconfig.JSONModuleObject(globalDNS, "name", globalDNS.(caddy.Module).CaddyModule().ID.Name(), nil)
 	}

+	// set up "global" (to the TLS app) DNS resolvers config
+	if globalResolvers, ok := options["tls_resolvers"]; ok && globalResolvers != nil {
+		tlsApp.Resolvers = globalResolvers.([]string)
+	}
+
 	// set up ECH from Caddyfile options
 	if ech, ok := options["ech"].(*caddytls.ECH); ok {
 		tlsApp.EncryptedClientHello = ech
@@ -595,6 +600,15 @@ func fillInGlobalACMEDefaults(issuer certmagic.Issuer, options map[string]any) e
 	if globalCertLifetime != nil && acmeIssuer.CertificateLifetime == 0 {
 		acmeIssuer.CertificateLifetime = globalCertLifetime.(caddy.Duration)
 	}
+	// apply global resolvers if DNS challenge is configured and resolvers are not already set
+	globalResolvers := options["tls_resolvers"]
+	if globalResolvers != nil && acmeIssuer.Challenges != nil && acmeIssuer.Challenges.DNS != nil {
+		// Check if DNS challenge is actually configured
+		hasDNSChallenge := globalACMEDNSok || acmeIssuer.Challenges.DNS.ProviderRaw != nil
+		if hasDNSChallenge && len(acmeIssuer.Challenges.DNS.Resolvers) == 0 {
+			acmeIssuer.Challenges.DNS.Resolvers = globalResolvers.([]string)
+		}
+	}
 	return nil
 }

@@ -151,7 +151,7 @@ func doHttpCallWithRetries(ctx caddy.Context, client *http.Client, request *http
 	var err error
 	const maxAttempts = 10

-	for i := 0; i < maxAttempts; i++ {
+	for i := range maxAttempts {
 		resp, err = attemptHttpCall(client, request)
 		if err != nil && i < maxAttempts-1 {
 			select {
@@ -1,6 +1,7 @@
 package caddytest

 import (
+	"bytes"
 	"net/http"
 	"strings"
 	"testing"
@@ -126,3 +127,118 @@ func TestLoadUnorderedJSON(t *testing.T) {
 	}
 	tester.AssertResponseCode(req, 200)
 }
+
+func TestCheckID(t *testing.T) {
+	tester := NewTester(t)
+	tester.InitServer(`{
+		"admin": {
+			"listen": "localhost:2999"
+		},
+		"apps": {
+			"http": {
+				"http_port": 9080,
+				"servers": {
+					"s_server": {
+						"@id": "s_server",
+						"listen": [
+							":9080"
+						],
+						"routes": [
+							{
+								"handle": [
+									{
+										"handler": "static_response",
+										"body": "Hello"
+									}
+								]
+							}
+						]
+					}
+				}
+			}
+		}
+	}
+	`, "json")
+	headers := []string{"Content-Type:application/json"}
+	sServer1 := []byte(`{"@id":"s_server","listen":[":9080"],"routes":[{"@id":"route1","handle":[{"handler":"static_response","body":"Hello 2"}]}]}`)
+
+	// PUT to an existing ID should fail with a 409 conflict
+	tester.AssertPutResponseBody(
+		"http://localhost:2999/id/s_server",
+		headers,
+		bytes.NewBuffer(sServer1),
+		409,
+		`{"error":"[/config/apps/http/servers/s_server] key already exists: s_server"}`+"\n")
+
+	// POST replaces the object fully
+	tester.AssertPostResponseBody(
+		"http://localhost:2999/id/s_server",
+		headers,
+		bytes.NewBuffer(sServer1),
+		200,
+		"")
+
+	// Verify the server is running the new route
+	tester.AssertGetResponse(
+		"http://localhost:9080/",
+		200,
+		"Hello 2")
+
+	// Update the existing route to ensure IDs are handled correctly when replaced
+	tester.AssertPostResponseBody(
+		"http://localhost:2999/id/s_server",
+		headers,
+		bytes.NewBuffer([]byte(`{"@id":"s_server","listen":[":9080"],"routes":[{"@id":"route1","handle":[{"handler":"static_response","body":"Hello2"}],"match":[{"path":["/route_1/*"]}]}]}`)),
+		200,
+		"")
+
+	sServer2 := []byte(`{"@id":"s_server","listen":[":9080"],"routes":[{"@id":"route1","handle":[{"handler":"static_response","body":"Hello2"}],"match":[{"path":["/route_1/*"]}]}]}`)
+
+	// Identical patch should succeed and return 200 (config is unchanged branch)
+	tester.AssertPatchResponseBody(
+		"http://localhost:2999/id/s_server",
+		headers,
+		bytes.NewBuffer(sServer2),
+		200,
+		"")
+
+	route2 := []byte(`{"@id":"route2","handle": [{"handler": "static_response","body": "route2"}],"match":[{"path":["/route_2/*"]}]}`)
+
+	// Put a new route2 object before the route1 object due to the path of /id/route1
+	// Being translated to: /config/apps/http/servers/s_server/routes/0
+	tester.AssertPutResponseBody(
+		"http://localhost:2999/id/route1",
+		headers,
+		bytes.NewBuffer(route2),
+		200,
+		"")
+
+	// Verify that the whole config looks correct, now containing both route1 and route2
+	tester.AssertGetResponse(
+		"http://localhost:2999/config/",
+		200,
+		`{"admin":{"listen":"localhost:2999"},"apps":{"http":{"http_port":9080,"servers":{"s_server":{"@id":"s_server","listen":[":9080"],"routes":[{"@id":"route2","handle":[{"body":"route2","handler":"static_response"}],"match":[{"path":["/route_2/*"]}]},{"@id":"route1","handle":[{"body":"Hello2","handler":"static_response"}],"match":[{"path":["/route_1/*"]}]}]}}}}}`+"\n")
+
+	// Try to add another copy of route2 using POST to test duplicate ID handling
+	// Since the first route2 ended up at array index 0, and we are appending to the array, the index for the new element would be 2
+	tester.AssertPostResponseBody(
+		"http://localhost:2999/id/route2",
+		headers,
+		bytes.NewBuffer(route2),
+		400,
+		`{"error":"indexing config: duplicate ID 'route2' found at /config/apps/http/servers/s_server/routes/0 and /config/apps/http/servers/s_server/routes/2"}`+"\n")
+
+	// Use PATCH to modify an existing object successfully
+	tester.AssertPatchResponseBody(
+		"http://localhost:2999/id/route1",
+		headers,
+		bytes.NewBuffer([]byte(`{"@id":"route1","handle":[{"handler":"static_response","body":"route1"}],"match":[{"path":["/route_1/*"]}]}`)),
+		200,
+		"")
+
+	// Verify the PATCH updated the server state
+	tester.AssertGetResponse(
+		"http://localhost:9080/route_1/",
+		200,
+		"route1")
+}
@@ -51,7 +51,7 @@ func TestACMEServerWithDefaults(t *testing.T) {
 		Client: &acme.Client{
 			Directory:  "https://acme.localhost:9443/acme/local/directory",
 			HTTPClient: tester.Client,
-			Logger:     slog.New(zapslog.NewHandler(logger.Core())),
+			Logger:     slog.New(zapslog.NewHandler(logger.Core(), zapslog.WithName("acmez"))),
 		},
 		ChallengeSolvers: map[string]acmez.Solver{
 			acme.ChallengeTypeHTTP01: &naiveHTTPSolver{logger: logger},
@@ -120,7 +120,7 @@ func TestACMEServerWithMismatchedChallenges(t *testing.T) {
 		Client: &acme.Client{
 			Directory:  "https://acme.localhost:9443/acme/local/directory",
 			HTTPClient: tester.Client,
-			Logger:     slog.New(zapslog.NewHandler(logger.Core())),
+			Logger:     slog.New(zapslog.NewHandler(logger.Core(), zapslog.WithName("acmez"))),
 		},
 		ChallengeSolvers: map[string]acmez.Solver{
 			acme.ChallengeTypeHTTP01: &naiveHTTPSolver{logger: logger},
@@ -143,3 +143,26 @@ func TestAutoHTTPRedirectsInsertedBeforeUserDefinedCatchAllWithNoExplicitHTTPSit
 	tester.AssertGetResponse("http://foo.localhost:9080/", 200, "Foo")
 	tester.AssertGetResponse("http://baz.localhost:9080/", 200, "Foo")
 }
+
+func TestAutoHTTPSRedirectSortingExactMatchOverWildcard(t *testing.T) {
+	tester := caddytest.NewTester(t)
+	tester.InitServer(`
+    {
+        skip_install_trust
+        admin localhost:2999
+        http_port     9080
+        https_port    9443
+        local_certs
+    }
+    *.localhost:10443 {
+        respond "Wildcard"
+    }
+    dev.localhost {
+        respond "Exact"
+    }
+  `, "caddyfile")
+
+	tester.AssertRedirect("http://dev.localhost:9080/", "https://dev.localhost/", http.StatusPermanentRedirect)
+
+	tester.AssertRedirect("http://foo.localhost:9080/", "https://foo.localhost:10443/", http.StatusPermanentRedirect)
+}
@@ -46,6 +46,18 @@ app.example.com {
 																		}
 																	]
 																},
+																{
+																	"handle": [
+																		{
+																			"handler": "headers",
+																			"request": {
+																				"delete": [
+																					"Remote-Email"
+																				]
+																			}
+																		}
+																	]
+																},
 																{
 																	"handle": [
 																		{
@@ -73,6 +85,18 @@ app.example.com {
 																		}
 																	]
 																},
+																{
+																	"handle": [
+																		{
+																			"handler": "headers",
+																			"request": {
+																				"delete": [
+																					"Remote-Groups"
+																				]
+																			}
+																		}
+																	]
+																},
 																{
 																	"handle": [
 																		{
@@ -100,6 +124,18 @@ app.example.com {
 																		}
 																	]
 																},
+																{
+																	"handle": [
+																		{
+																			"handler": "headers",
+																			"request": {
+																				"delete": [
+																					"Remote-Name"
+																				]
+																			}
+																		}
+																	]
+																},
 																{
 																	"handle": [
 																		{
@@ -127,6 +163,18 @@ app.example.com {
 																		}
 																	]
 																},
+																{
+																	"handle": [
+																		{
+																			"handler": "headers",
+																			"request": {
+																				"delete": [
+																					"Remote-User"
+																				]
+																			}
+																		}
+																	]
+																},
 																{
 																	"handle": [
 																		{
@@ -200,4 +248,4 @@ app.example.com {
 			}
 		}
 	}
-}
+}
@@ -0,0 +1,146 @@
+:8080
+
+forward_auth 127.0.0.1:9091 {
+	uri /
+	copy_headers X-User-Id X-User-Role
+}
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":8080"
+					],
+					"routes": [
+						{
+							"handle": [
+								{
+									"handle_response": [
+										{
+											"match": {
+												"status_code": [
+													2
+												]
+											},
+											"routes": [
+												{
+													"handle": [
+														{
+															"handler": "vars"
+														}
+													]
+												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"delete": [
+																	"X-User-Id"
+																]
+															}
+														}
+													]
+												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"set": {
+																	"X-User-Id": [
+																		"{http.reverse_proxy.header.X-User-Id}"
+																	]
+																}
+															}
+														}
+													],
+													"match": [
+														{
+															"not": [
+																{
+																	"vars": {
+																		"{http.reverse_proxy.header.X-User-Id}": [
+																			""
+																		]
+																	}
+																}
+															]
+														}
+													]
+												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"delete": [
+																	"X-User-Role"
+																]
+															}
+														}
+													]
+												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"set": {
+																	"X-User-Role": [
+																		"{http.reverse_proxy.header.X-User-Role}"
+																	]
+																}
+															}
+														}
+													],
+													"match": [
+														{
+															"not": [
+																{
+																	"vars": {
+																		"{http.reverse_proxy.header.X-User-Role}": [
+																			""
+																		]
+																	}
+																}
+															]
+														}
+													]
+												}
+											]
+										}
+									],
+									"handler": "reverse_proxy",
+									"headers": {
+										"request": {
+											"set": {
+												"X-Forwarded-Method": [
+													"{http.request.method}"
+												],
+												"X-Forwarded-Uri": [
+													"{http.request.uri}"
+												]
+											}
+										}
+									},
+									"rewrite": {
+										"method": "GET",
+										"uri": "/"
+									},
+									"upstreams": [
+										{
+											"dial": "127.0.0.1:9091"
+										}
+									]
+								}
+							]
+						}
+					]
+				}
+			}
+		}
+	}
+}
@@ -35,6 +35,18 @@ forward_auth localhost:9000 {
 														}
 													]
 												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"delete": [
+																	"1"
+																]
+															}
+														}
+													]
+												},
 												{
 													"handle": [
 														{
@@ -62,6 +74,18 @@ forward_auth localhost:9000 {
 														}
 													]
 												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"delete": [
+																	"B"
+																]
+															}
+														}
+													]
+												},
 												{
 													"handle": [
 														{
@@ -89,6 +113,18 @@ forward_auth localhost:9000 {
 														}
 													]
 												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"delete": [
+																	"3"
+																]
+															}
+														}
+													]
+												},
 												{
 													"handle": [
 														{
@@ -116,6 +152,18 @@ forward_auth localhost:9000 {
 														}
 													]
 												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"delete": [
+																	"D"
+																]
+															}
+														}
+													]
+												},
 												{
 													"handle": [
 														{
@@ -143,6 +191,18 @@ forward_auth localhost:9000 {
 														}
 													]
 												},
+												{
+													"handle": [
+														{
+															"handler": "headers",
+															"request": {
+																"delete": [
+																	"5"
+																]
+															}
+														}
+													]
+												},
 												{
 													"handle": [
 														{
@@ -203,4 +263,4 @@ forward_auth localhost:9000 {
 			}
 		}
 	}
-}
+}
@@ -0,0 +1,77 @@
+{
+	email test@example.com
+	dns mock
+	tls_resolvers 1.1.1.1 8.8.8.8
+	acme_dns
+}
+
+example.com {
+}
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":443"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"host": [
+										"example.com"
+									]
+								}
+							],
+							"terminal": true
+						}
+					]
+				}
+			}
+		},
+		"tls": {
+			"automation": {
+				"policies": [
+					{
+						"issuers": [
+							{
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"1.1.1.1",
+											"8.8.8.8"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							},
+							{
+								"ca": "https://acme.zerossl.com/v2/DV90",
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"1.1.1.1",
+											"8.8.8.8"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							}
+						]
+					}
+				]
+			},
+			"dns": {
+				"name": "mock"
+			},
+			"resolvers": [
+				"1.1.1.1",
+				"8.8.8.8"
+			]
+		}
+	}
+}
@@ -0,0 +1,38 @@
+{
+	tls_resolvers 1.1.1.1 8.8.8.8
+}
+
+example.com {
+}
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":443"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"host": [
+										"example.com"
+									]
+								}
+							],
+							"terminal": true
+						}
+					]
+				}
+			}
+		},
+		"tls": {
+			"resolvers": [
+				"1.1.1.1",
+				"8.8.8.8"
+			]
+		}
+	}
+}
@@ -0,0 +1,72 @@
+{
+	email test@example.com
+	dns mock
+	tls_resolvers 1.1.1.1 8.8.8.8
+}
+
+example.com {
+	tls {
+		dns mock
+	}
+}
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":443"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"host": [
+										"example.com"
+									]
+								}
+							],
+							"terminal": true
+						}
+					]
+				}
+			}
+		},
+		"tls": {
+			"automation": {
+				"policies": [
+					{
+						"subjects": [
+							"example.com"
+						],
+						"issuers": [
+							{
+								"challenges": {
+									"dns": {
+										"provider": {
+											"name": "mock"
+										},
+										"resolvers": [
+											"1.1.1.1",
+											"8.8.8.8"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							}
+						]
+					}
+				]
+			},
+			"dns": {
+				"name": "mock"
+			},
+			"resolvers": [
+				"1.1.1.1",
+				"8.8.8.8"
+			]
+		}
+	}
+}
@@ -0,0 +1,98 @@
+{
+	email test@example.com
+	dns mock
+	tls_resolvers 1.1.1.1 8.8.8.8
+	acme_dns
+}
+
+example.com {
+	tls {
+		resolvers 9.9.9.9
+	}
+}
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":443"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"host": [
+										"example.com"
+									]
+								}
+							],
+							"terminal": true
+						}
+					]
+				}
+			}
+		},
+		"tls": {
+			"automation": {
+				"policies": [
+					{
+						"subjects": [
+							"example.com"
+						],
+						"issuers": [
+							{
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"9.9.9.9"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							}
+						]
+					},
+					{
+						"issuers": [
+							{
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"1.1.1.1",
+											"8.8.8.8"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							},
+							{
+								"ca": "https://acme.zerossl.com/v2/DV90",
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"1.1.1.1",
+											"8.8.8.8"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							}
+						]
+					}
+				]
+			},
+			"dns": {
+				"name": "mock"
+			},
+			"resolvers": [
+				"1.1.1.1",
+				"8.8.8.8"
+			]
+		}
+	}
+}
@@ -0,0 +1,112 @@
+{
+	email test@example.com
+	dns mock
+	tls_resolvers 1.1.1.1 8.8.8.8
+	acme_dns
+}
+
+site1.example.com {
+}
+
+site2.example.com {
+	tls {
+		resolvers 9.9.9.9 8.8.4.4
+	}
+}
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":443"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"host": [
+										"site1.example.com"
+									]
+								}
+							],
+							"terminal": true
+						},
+						{
+							"match": [
+								{
+									"host": [
+										"site2.example.com"
+									]
+								}
+							],
+							"terminal": true
+						}
+					]
+				}
+			}
+		},
+		"tls": {
+			"automation": {
+				"policies": [
+					{
+						"subjects": [
+							"site2.example.com"
+						],
+						"issuers": [
+							{
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"9.9.9.9",
+											"8.8.4.4"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							}
+						]
+					},
+					{
+						"issuers": [
+							{
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"1.1.1.1",
+											"8.8.8.8"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							},
+							{
+								"ca": "https://acme.zerossl.com/v2/DV90",
+								"challenges": {
+									"dns": {
+										"resolvers": [
+											"1.1.1.1",
+											"8.8.8.8"
+										]
+									}
+								},
+								"email": "test@example.com",
+								"module": "acme"
+							}
+						]
+					}
+				]
+			},
+			"dns": {
+				"name": "mock"
+			},
+			"resolvers": [
+				"1.1.1.1",
+				"8.8.8.8"
+			]
+		}
+	}
+}
@@ -0,0 +1,52 @@
+import testdata/issue_7518_unused_block_panic_snippets.conf
+
+example.com {
+	import snippet
+}
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":443"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"host": [
+										"example.com"
+									]
+								}
+							],
+							"handle": [
+								{
+									"handler": "subroute",
+									"routes": [
+										{
+											"handle": [
+												{
+													"handler": "headers",
+													"response": {
+														"set": {
+															"Reverse_proxy": [
+																"localhost:3000"
+															]
+														}
+													}
+												}
+											]
+										}
+									]
+								}
+							],
+							"terminal": true
+						}
+					]
+				}
+			}
+		}
+	}
+}
@@ -1,27 +1,47 @@
 :80

-log {
+log one {
 	output file /var/log/access.log {
+		mode 0644
+		dir_mode 0755
 		roll_size 1gb
 		roll_uncompressed
+		roll_compression none
 		roll_local_time
 		roll_keep 5
 		roll_keep_for 90d
 	}
 }
+log two {
+	output file /var/log/access-2.log {
+		mode 0777
+		dir_mode from_file
+		roll_size 1gib
+		roll_compression zstd
+		roll_interval 12h
+		roll_at 00:00 06:00 12:00,18:00
+		roll_minutes 10 40 45,46
+		roll_keep 10
+		roll_keep_for 90d
+	}
+}
 ----------
 {
 	"logging": {
 		"logs": {
 			"default": {
 				"exclude": [
-					"http.log.access.log0"
+					"http.log.access.one",
+					"http.log.access.two"
 				]
 			},
-			"log0": {
+			"one": {
 				"writer": {
+					"dir_mode": "0755",
 					"filename": "/var/log/access.log",
+					"mode": "0644",
 					"output": "file",
+					"roll_compression": "none",
 					"roll_gzip": false,
 					"roll_keep": 5,
 					"roll_keep_days": 90,
@@ -29,7 +49,35 @@ log {
 					"roll_size_mb": 954
 				},
 				"include": [
-					"http.log.access.log0"
+					"http.log.access.one"
+				]
+			},
+			"two": {
+				"writer": {
+					"dir_mode": "from_file",
+					"filename": "/var/log/access-2.log",
+					"mode": "0777",
+					"output": "file",
+					"roll_at": [
+						"00:00",
+						"06:00",
+						"12:00",
+						"18:00"
+					],
+					"roll_compression": "zstd",
+					"roll_interval": 43200000000000,
+					"roll_keep": 10,
+					"roll_keep_days": 90,
+					"roll_minutes": [
+						10,
+						40,
+						45,
+						46
+					],
+					"roll_size_mb": 1024
+				},
+				"include": [
+					"http.log.access.two"
 				]
 			}
 		}
@@ -42,7 +90,7 @@ log {
 						":80"
 					],
 					"logs": {
-						"default_logger_name": "log0"
+						"default_logger_name": "two"
 					}
 				}
 			}
@@ -0,0 +1,206 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package integration
+
+import (
+	"fmt"
+	"net/http"
+	"net/http/httptest"
+	"strings"
+	"sync"
+	"testing"
+
+	"github.com/caddyserver/caddy/v2/caddytest"
+)
+
+// TestForwardAuthCopyHeadersStripsClientHeaders is a regression test for the
+// header injection vulnerability in forward_auth copy_headers.
+//
+// When the auth service returns 200 OK without one of the copy_headers headers,
+// the MatchNot guard skips the Set operation. Before this fix, the original
+// client-supplied header survived unchanged into the backend request, allowing
+// privilege escalation with only a valid (non-privileged) bearer token. After
+// the fix, an unconditional delete route runs first, so the backend always
+// sees an absent header rather than the attacker-supplied value.
+func TestForwardAuthCopyHeadersStripsClientHeaders(t *testing.T) {
+	// Mock auth service: accepts any Bearer token, returns 200 OK with NO
+	// identity headers. This is the stateless JWT validator pattern that
+	// triggers the vulnerability.
+	authSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if strings.HasPrefix(r.Header.Get("Authorization"), "Bearer ") {
+			w.WriteHeader(http.StatusOK)
+			return
+		}
+		w.WriteHeader(http.StatusUnauthorized)
+	}))
+	defer authSrv.Close()
+
+	// Mock backend: records the identity headers it receives. A real application
+	// would use X-User-Id / X-User-Role to make authorization decisions.
+	type received struct{ userID, userRole string }
+	var (
+		mu   sync.Mutex
+		last received
+	)
+	backendSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		mu.Lock()
+		last = received{
+			userID:   r.Header.Get("X-User-Id"),
+			userRole: r.Header.Get("X-User-Role"),
+		}
+		mu.Unlock()
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprint(w, "ok")
+	}))
+	defer backendSrv.Close()
+
+	authAddr := strings.TrimPrefix(authSrv.URL, "http://")
+	backendAddr := strings.TrimPrefix(backendSrv.URL, "http://")
+
+	tester := caddytest.NewTester(t)
+	tester.InitServer(fmt.Sprintf(`
+	{
+		skip_install_trust
+		admin localhost:2999
+		http_port 9080
+		https_port 9443
+		grace_period 1ns
+	}
+	http://localhost:9080 {
+		forward_auth %s {
+			uri /
+			copy_headers X-User-Id X-User-Role
+		}
+		reverse_proxy %s
+	}
+	`, authAddr, backendAddr), "caddyfile")
+
+	// Case 1: no token. Auth must still reject the request even when the client
+	// includes identity headers. This confirms the auth check is not bypassed.
+	req, _ := http.NewRequest(http.MethodGet, "http://localhost:9080/", nil)
+	req.Header.Set("X-User-Id", "injected")
+	req.Header.Set("X-User-Role", "injected")
+	resp := tester.AssertResponseCode(req, http.StatusUnauthorized)
+	resp.Body.Close()
+
+	// Case 2: valid token, no injected headers. The backend should see absent
+	// identity headers (the auth service never returns them).
+	req, _ = http.NewRequest(http.MethodGet, "http://localhost:9080/", nil)
+	req.Header.Set("Authorization", "Bearer token123")
+	tester.AssertResponse(req, http.StatusOK, "ok")
+	mu.Lock()
+	gotID, gotRole := last.userID, last.userRole
+	mu.Unlock()
+	if gotID != "" {
+		t.Errorf("baseline: X-User-Id should be absent, got %q", gotID)
+	}
+	if gotRole != "" {
+		t.Errorf("baseline: X-User-Role should be absent, got %q", gotRole)
+	}
+
+	// Case 3 (the security regression): valid token plus forged identity headers.
+	// The fix must strip those values so the backend never sees them.
+	req, _ = http.NewRequest(http.MethodGet, "http://localhost:9080/", nil)
+	req.Header.Set("Authorization", "Bearer token123")
+	req.Header.Set("X-User-Id", "admin")        // forged
+	req.Header.Set("X-User-Role", "superadmin") // forged
+	tester.AssertResponse(req, http.StatusOK, "ok")
+	mu.Lock()
+	gotID, gotRole = last.userID, last.userRole
+	mu.Unlock()
+	if gotID != "" {
+		t.Errorf("injection: X-User-Id must be stripped, got %q", gotID)
+	}
+	if gotRole != "" {
+		t.Errorf("injection: X-User-Role must be stripped, got %q", gotRole)
+	}
+}
+
+// TestForwardAuthCopyHeadersAuthResponseWins verifies that when the auth
+// service does include a copy_headers header in its response, that value
+// is forwarded to the backend and takes precedence over any client-supplied
+// value for the same header.
+func TestForwardAuthCopyHeadersAuthResponseWins(t *testing.T) {
+	const wantUserID = "service-user-42"
+	const wantUserRole = "editor"
+
+	// Auth service: accepts bearer token and sets identity headers.
+	authSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if strings.HasPrefix(r.Header.Get("Authorization"), "Bearer ") {
+			w.Header().Set("X-User-Id", wantUserID)
+			w.Header().Set("X-User-Role", wantUserRole)
+			w.WriteHeader(http.StatusOK)
+			return
+		}
+		w.WriteHeader(http.StatusUnauthorized)
+	}))
+	defer authSrv.Close()
+
+	type received struct{ userID, userRole string }
+	var (
+		mu   sync.Mutex
+		last received
+	)
+	backendSrv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		mu.Lock()
+		last = received{
+			userID:   r.Header.Get("X-User-Id"),
+			userRole: r.Header.Get("X-User-Role"),
+		}
+		mu.Unlock()
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprint(w, "ok")
+	}))
+	defer backendSrv.Close()
+
+	authAddr := strings.TrimPrefix(authSrv.URL, "http://")
+	backendAddr := strings.TrimPrefix(backendSrv.URL, "http://")
+
+	tester := caddytest.NewTester(t)
+	tester.InitServer(fmt.Sprintf(`
+	{
+		skip_install_trust
+		admin localhost:2999
+		http_port 9080
+		https_port 9443
+		grace_period 1ns
+	}
+	http://localhost:9080 {
+		forward_auth %s {
+			uri /
+			copy_headers X-User-Id X-User-Role
+		}
+		reverse_proxy %s
+	}
+	`, authAddr, backendAddr), "caddyfile")
+
+	// The client sends forged headers; the auth service overrides them with
+	// its own values. The backend must receive the auth service values.
+	req, _ := http.NewRequest(http.MethodGet, "http://localhost:9080/", nil)
+	req.Header.Set("Authorization", "Bearer token123")
+	req.Header.Set("X-User-Id", "forged-id")   // must be overwritten
+	req.Header.Set("X-User-Role", "forged-role") // must be overwritten
+	tester.AssertResponse(req, http.StatusOK, "ok")
+
+	mu.Lock()
+	gotID, gotRole := last.userID, last.userRole
+	mu.Unlock()
+	if gotID != wantUserID {
+		t.Errorf("X-User-Id: want %q, got %q", wantUserID, gotID)
+	}
+	if gotRole != wantUserRole {
+		t.Errorf("X-User-Role: want %q, got %q", wantUserRole, gotRole)
+	}
+}
@@ -0,0 +1,595 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+// Integration tests for Caddy's PROXY protocol support, covering two distinct
+// roles that Caddy can play:
+//
+//  1. As a PROXY protocol *sender* (reverse proxy outbound transport):
+//     Caddy receives an inbound request from a test client and the
+//     reverse_proxy handler forwards it to an upstream with a PROXY protocol
+//     header (v1 or v2) prepended to the connection.  A lightweight backend
+//     built with go-proxyproto validates that the header was received and
+//     carries the correct client address.
+//
+//     Transport versions tested:
+//   - "1.1"  -> plain HTTP/1.1 to the upstream
+//   - "h2c"  -> HTTP/2 cleartext (h2c) to the upstream (regression for #7529)
+//   - "2"    -> HTTP/2 over TLS (h2) to the upstream
+//
+//     For each transport version both PROXY protocol v1 and v2 are exercised.
+//
+//     HTTP/3 (h3) is not included because it uses QUIC/UDP and therefore
+//     bypasses the TCP-level dialContext that injects PROXY protocol headers;
+//     there is no meaningful h3 + proxy protocol sender combination to test.
+//
+//  2. As a PROXY protocol *receiver* (server-side listener wrapper):
+//     A raw TCP client dials Caddy directly, injects a PROXY v2 header
+//     spoofing a source address, and sends a normal HTTP/1.1 request.  The
+//     Caddy server is configured with the proxy_protocol listener wrapper and
+//     is expected to surface the spoofed address via the
+//     {http.request.remote.host} placeholder.
+
+package integration
+
+import (
+	"crypto/tls"
+	"encoding/json"
+	"fmt"
+	"net"
+	"net/http"
+	"net/http/httptest"
+	"slices"
+	"strings"
+	"sync"
+	"testing"
+
+	goproxy "github.com/pires/go-proxyproto"
+	"golang.org/x/net/http2"
+	"golang.org/x/net/http2/h2c"
+
+	"github.com/caddyserver/caddy/v2/caddytest"
+)
+
+// proxyProtoBackend is a minimal HTTP server that sits behind a
+// go-proxyproto listener and records the source address that was
+// delivered in the PROXY header for each request.
+type proxyProtoBackend struct {
+	mu          sync.Mutex
+	headerAddrs []string // host:port strings extracted from each PROXY header
+
+	ln  net.Listener
+	srv *http.Server
+}
+
+// newProxyProtoBackend starts a TCP listener wrapped with go-proxyproto on a
+// random local port and serves requests with a simple "OK" body.  The PROXY
+// header source addresses are accumulated in headerAddrs so tests can
+// inspect them.
+func newProxyProtoBackend(t *testing.T) *proxyProtoBackend {
+	t.Helper()
+
+	b := &proxyProtoBackend{}
+
+	rawLn, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("backend: listen: %v", err)
+	}
+
+	// Wrap with go-proxyproto so the PROXY header is stripped and parsed
+	// before the HTTP server sees the connection.  We use REQUIRE so that a
+	// missing header returns an error instead of silently passing through.
+	pLn := &goproxy.Listener{
+		Listener: rawLn,
+		Policy: func(_ net.Addr) (goproxy.Policy, error) {
+			return goproxy.REQUIRE, nil
+		},
+	}
+	b.ln = pLn
+
+	// Wrap the handler with h2c support so the backend can speak HTTP/2
+	// cleartext (h2c) as well as plain HTTP/1.1.  Without this, Caddy's
+	// reverse proxy would receive a 'frame too large' error when the
+	// upstream transport is configured to use h2c.
+	h2Server := &http2.Server{}
+	handlerFn := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// go-proxyproto has already updated the net.Conn's remote
+		// address to the value from the PROXY header; the HTTP server
+		// surfaces it in r.RemoteAddr.
+		b.mu.Lock()
+		b.headerAddrs = append(b.headerAddrs, r.RemoteAddr)
+		b.mu.Unlock()
+		w.WriteHeader(http.StatusOK)
+		_, _ = fmt.Fprint(w, "OK")
+	})
+
+	b.srv = &http.Server{
+		Handler: h2c.NewHandler(handlerFn, h2Server),
+	}
+
+	go b.srv.Serve(pLn) //nolint:errcheck
+	t.Cleanup(func() {
+		_ = b.srv.Close()
+		_ = rawLn.Close()
+	})
+
+	return b
+}
+
+// addr returns the listening address (host:port) of the backend.
+func (b *proxyProtoBackend) addr() string {
+	return b.ln.Addr().String()
+}
+
+// recordedAddrs returns a snapshot of all PROXY-header source addresses seen
+// so far.
+func (b *proxyProtoBackend) recordedAddrs() []string {
+	b.mu.Lock()
+	defer b.mu.Unlock()
+	cp := make([]string, len(b.headerAddrs))
+	copy(cp, b.headerAddrs)
+	return cp
+}
+
+// tlsProxyProtoBackend is a TLS-enabled backend that sits behind a
+// go-proxyproto listener.  The PROXY header is stripped before the TLS
+// handshake so the layer order on a connection is:
+//
+//	raw TCP → go-proxyproto (strips PROXY header) → TLS handshake → HTTP/2
+type tlsProxyProtoBackend struct {
+	mu          sync.Mutex
+	headerAddrs []string
+
+	srv *httptest.Server
+}
+
+// newTLSProxyProtoBackend starts a TLS listener that first reads and strips
+// PROXY protocol headers (go-proxyproto, REQUIRE policy) and then performs a
+// TLS handshake.  The backend speaks HTTP/2 over TLS (h2).
+//
+// The certificate is the standard self-signed certificate generated by
+// httptest.Server; the Caddy transport must be configured with
+// insecure_skip_verify: true to trust it.
+func newTLSProxyProtoBackend(t *testing.T) *tlsProxyProtoBackend {
+	t.Helper()
+
+	b := &tlsProxyProtoBackend{}
+
+	handlerFn := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		b.mu.Lock()
+		b.headerAddrs = append(b.headerAddrs, r.RemoteAddr)
+		b.mu.Unlock()
+		w.WriteHeader(http.StatusOK)
+		_, _ = fmt.Fprint(w, "OK")
+	})
+
+	rawLn, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("tlsBackend: listen: %v", err)
+	}
+
+	// Wrap with go-proxyproto so the PROXY header is consumed before TLS.
+	pLn := &goproxy.Listener{
+		Listener: rawLn,
+		Policy: func(_ net.Addr) (goproxy.Policy, error) {
+			return goproxy.REQUIRE, nil
+		},
+	}
+
+	// httptest.NewUnstartedServer lets us replace the listener before
+	// calling StartTLS(), which wraps our proxyproto listener with
+	// tls.NewListener.  This gives us the right layer order.
+	b.srv = httptest.NewUnstartedServer(handlerFn)
+	b.srv.Listener = pLn
+
+	// StartTLS enables HTTP/2 on the server automatically.
+	b.srv.StartTLS()
+
+	t.Cleanup(func() {
+		b.srv.Close()
+	})
+
+	return b
+}
+
+// addr returns the listening address (host:port) of the TLS backend.
+func (b *tlsProxyProtoBackend) addr() string {
+	return b.srv.Listener.Addr().String()
+}
+
+// tlsConfig returns the *tls.Config used by the backend server.
+// Tests can use it to verify cert details if needed.
+func (b *tlsProxyProtoBackend) tlsConfig() *tls.Config {
+	return b.srv.TLS
+}
+
+// recordedAddrs returns a snapshot of all PROXY-header source addresses.
+func (b *tlsProxyProtoBackend) recordedAddrs() []string {
+	b.mu.Lock()
+	defer b.mu.Unlock()
+	cp := make([]string, len(b.headerAddrs))
+	copy(cp, b.headerAddrs)
+	return cp
+}
+
+// proxyProtoTLSConfig builds a Caddy JSON configuration that proxies to a TLS
+// upstream with PROXY protocol.  The transport uses insecure_skip_verify so
+// the self-signed certificate generated by httptest.Server is accepted.
+func proxyProtoTLSConfig(listenPort int, backendAddr, ppVersion string, transportVersions []string) string {
+	versionsJSON, _ := json.Marshal(transportVersions)
+	return fmt.Sprintf(`{
+		"admin": {
+			"listen": "localhost:2999"
+		},
+		"apps": {
+			"pki": {
+				"certificate_authorities": {
+					"local": {
+						"install_trust": false
+					}
+				}
+			},
+			"http": {
+				"grace_period": 1,
+				"servers": {
+					"proxy": {
+						"listen": [":%d"],
+						"automatic_https": {
+							"disable": true
+						},
+						"routes": [
+							{
+								"handle": [
+									{
+										"handler": "reverse_proxy",
+										"upstreams": [{"dial": "%s"}],
+										"transport": {
+											"protocol": "http",
+											"proxy_protocol": "%s",
+											"versions": %s,
+											"tls": {
+												"insecure_skip_verify": true
+											}
+										}
+									}
+								]
+							}
+						]
+					}
+				}
+			}
+		}
+	}`, listenPort, backendAddr, ppVersion, string(versionsJSON))
+}
+
+// testTLSProxyProtocolMatrix is the shared implementation for TLS-based proxy
+// protocol tests.  It mirrors testProxyProtocolMatrix but uses a TLS backend.
+func testTLSProxyProtocolMatrix(t *testing.T, ppVersion string, transportVersions []string, numRequests int) {
+	t.Helper()
+
+	backend := newTLSProxyProtoBackend(t)
+	listenPort := freePort(t)
+
+	tester := caddytest.NewTester(t)
+	tester.WithDefaultOverrides(caddytest.Config{
+		AdminPort: 2999,
+	})
+	cfg := proxyProtoTLSConfig(listenPort, backend.addr(), ppVersion, transportVersions)
+	tester.InitServer(cfg, "json")
+
+	proxyURL := fmt.Sprintf("http://127.0.0.1:%d/", listenPort)
+
+	for i := 0; i < numRequests; i++ {
+		resp, err := tester.Client.Get(proxyURL)
+		if err != nil {
+			t.Fatalf("request %d/%d: GET %s: %v", i+1, numRequests, proxyURL, err)
+		}
+		resp.Body.Close()
+		if resp.StatusCode != http.StatusOK {
+			t.Errorf("request %d/%d: expected status 200, got %d", i+1, numRequests, resp.StatusCode)
+		}
+	}
+
+	addrs := backend.recordedAddrs()
+	if len(addrs) == 0 {
+		t.Fatalf("backend recorded no PROXY protocol addresses (expected at least 1)")
+	}
+
+	for i, addr := range addrs {
+		host, _, err := net.SplitHostPort(addr)
+		if err != nil {
+			t.Errorf("addr[%d] %q: SplitHostPort: %v", i, addr, err)
+			continue
+		}
+		if host != "127.0.0.1" {
+			t.Errorf("addr[%d]: expected source 127.0.0.1, got %q", i, host)
+		}
+	}
+}
+
+// proxyProtoConfig builds a Caddy JSON configuration that:
+//   - listens on listenPort for inbound HTTP requests
+//   - proxies them to backendAddr with PROXY protocol ppVersion ("v1"/"v2")
+//   - uses the given transport versions (e.g. ["1.1"] or ["h2c"])
+func proxyProtoConfig(listenPort int, backendAddr, ppVersion string, transportVersions []string) string {
+	versionsJSON, _ := json.Marshal(transportVersions)
+	return fmt.Sprintf(`{
+		"admin": {
+			"listen": "localhost:2999"
+		},
+		"apps": {
+			"pki": {
+				"certificate_authorities": {
+					"local": {
+						"install_trust": false
+					}
+				}
+			},
+			"http": {
+				"grace_period": 1,
+				"servers": {
+					"proxy": {
+						"listen": [":%d"],
+						"automatic_https": {
+							"disable": true
+						},
+						"routes": [
+							{
+								"handle": [
+									{
+										"handler": "reverse_proxy",
+										"upstreams": [{"dial": "%s"}],
+										"transport": {
+											"protocol": "http",
+											"proxy_protocol": "%s",
+											"versions": %s
+										}
+									}
+								]
+							}
+						]
+					}
+				}
+			}
+		}
+	}`, listenPort, backendAddr, ppVersion, string(versionsJSON))
+}
+
+// freePort returns a free local TCP port by binding briefly and releasing it.
+func freePort(t *testing.T) int {
+	t.Helper()
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("freePort: %v", err)
+	}
+	port := ln.Addr().(*net.TCPAddr).Port
+	_ = ln.Close()
+	return port
+}
+
+// TestProxyProtocolV1WithH1 verifies that PROXY protocol v1 headers are sent
+// correctly when the transport uses HTTP/1.1 to the upstream.
+func TestProxyProtocolV1WithH1(t *testing.T) {
+	testProxyProtocolMatrix(t, "v1", []string{"1.1"}, 1)
+}
+
+// TestProxyProtocolV2WithH1 verifies that PROXY protocol v2 headers are sent
+// correctly when the transport uses HTTP/1.1 to the upstream.
+func TestProxyProtocolV2WithH1(t *testing.T) {
+	testProxyProtocolMatrix(t, "v2", []string{"1.1"}, 1)
+}
+
+// TestProxyProtocolV1WithH2C verifies that PROXY protocol v1 headers are sent
+// correctly when the transport uses h2c (HTTP/2 cleartext) to the upstream.
+func TestProxyProtocolV1WithH2C(t *testing.T) {
+	testProxyProtocolMatrix(t, "v1", []string{"h2c"}, 1)
+}
+
+// TestProxyProtocolV2WithH2C verifies that PROXY protocol v2 headers are sent
+// correctly when the transport uses h2c (HTTP/2 cleartext) to the upstream.
+// This is the primary regression test for github.com/caddyserver/caddy/issues/7529:
+// before the fix, the h2 transport opened a new TCP connection per request
+// (because req.URL.Host was mangled differently for each request due to the
+// varying client port), which caused file-descriptor exhaustion under load.
+func TestProxyProtocolV2WithH2C(t *testing.T) {
+	testProxyProtocolMatrix(t, "v2", []string{"h2c"}, 1)
+}
+
+// TestProxyProtocolV2WithH2CMultipleRequests sends several sequential requests
+// through the h2c + PROXY-protocol path and confirms that:
+//  1. Every request receives a 200 response (no connection exhaustion).
+//  2. The backend received at least one PROXY header (connection was reused).
+//
+// This is the core regression guard for issue #7529: without the fix, a new
+// TCP connection was opened per request, quickly exhausting file descriptors.
+func TestProxyProtocolV2WithH2CMultipleRequests(t *testing.T) {
+	testProxyProtocolMatrix(t, "v2", []string{"h2c"}, 5)
+}
+
+// TestProxyProtocolV1WithH2 verifies that PROXY protocol v1 headers are sent
+// correctly when the transport uses HTTP/2 over TLS (h2) to the upstream.
+func TestProxyProtocolV1WithH2(t *testing.T) {
+	testTLSProxyProtocolMatrix(t, "v1", []string{"2"}, 1)
+}
+
+// TestProxyProtocolV2WithH2 verifies that PROXY protocol v2 headers are sent
+// correctly when the transport uses HTTP/2 over TLS (h2) to the upstream.
+func TestProxyProtocolV2WithH2(t *testing.T) {
+	testTLSProxyProtocolMatrix(t, "v2", []string{"2"}, 1)
+}
+
+// TestProxyProtocolServerAndProxy is an end-to-end matrix test that exercises
+// all combinations of PROXY protocol version x transport version.
+func TestProxyProtocolServerAndProxy(t *testing.T) {
+	plainTests := []struct {
+		name              string
+		ppVersion         string
+		transportVersions []string
+		numRequests       int
+	}{
+		{"h1-v1", "v1", []string{"1.1"}, 3},
+		{"h1-v2", "v2", []string{"1.1"}, 3},
+		{"h2c-v1", "v1", []string{"h2c"}, 3},
+		{"h2c-v2", "v2", []string{"h2c"}, 3},
+	}
+	for _, tc := range plainTests {
+		t.Run(tc.name, func(t *testing.T) {
+			testProxyProtocolMatrix(t, tc.ppVersion, tc.transportVersions, tc.numRequests)
+		})
+	}
+
+	tlsTests := []struct {
+		name              string
+		ppVersion         string
+		transportVersions []string
+		numRequests       int
+	}{
+		{"h2-v1", "v1", []string{"2"}, 3},
+		{"h2-v2", "v2", []string{"2"}, 3},
+	}
+	for _, tc := range tlsTests {
+		t.Run(tc.name, func(t *testing.T) {
+			testTLSProxyProtocolMatrix(t, tc.ppVersion, tc.transportVersions, tc.numRequests)
+		})
+	}
+}
+
+// testProxyProtocolMatrix is the shared implementation for the proxy protocol
+// tests.  It:
+//  1. Starts a go-proxyproto-wrapped backend.
+//  2. Configures Caddy as a reverse proxy with the given PROXY protocol
+//     version and transport versions.
+//  3. Sends numRequests GET requests through Caddy and asserts 200 OK each time.
+//  4. Asserts the backend recorded at least one PROXY header whose source host
+//     is 127.0.0.1 (the loopback address used by the test client).
+func testProxyProtocolMatrix(t *testing.T, ppVersion string, transportVersions []string, numRequests int) {
+	t.Helper()
+
+	backend := newProxyProtoBackend(t)
+	listenPort := freePort(t)
+
+	tester := caddytest.NewTester(t)
+	tester.WithDefaultOverrides(caddytest.Config{
+		AdminPort: 2999,
+	})
+	cfg := proxyProtoConfig(listenPort, backend.addr(), ppVersion, transportVersions)
+	tester.InitServer(cfg, "json")
+
+	// If the test is h2c-only (no "1.1" in versions), reconfigure the test
+	// client transport to use unencrypted HTTP/2 so we actually exercise the
+	// h2c code path through Caddy.
+	if slices.Contains(transportVersions, "h2c") && !slices.Contains(transportVersions, "1.1") {
+		tr, ok := tester.Client.Transport.(*http.Transport)
+		if ok {
+			tr.Protocols = new(http.Protocols)
+			tr.Protocols.SetHTTP1(false)
+			tr.Protocols.SetUnencryptedHTTP2(true)
+		}
+	}
+
+	proxyURL := fmt.Sprintf("http://127.0.0.1:%d/", listenPort)
+
+	for i := 0; i < numRequests; i++ {
+		resp, err := tester.Client.Get(proxyURL)
+		if err != nil {
+			t.Fatalf("request %d/%d: GET %s: %v", i+1, numRequests, proxyURL, err)
+		}
+		resp.Body.Close()
+		if resp.StatusCode != http.StatusOK {
+			t.Errorf("request %d/%d: expected status 200, got %d", i+1, numRequests, resp.StatusCode)
+		}
+	}
+
+	// The backend must have seen at least one PROXY header.  For h1, there is
+	// one per request; for h2c, requests share the same connection so only one
+	// header is written at connection establishment.
+	addrs := backend.recordedAddrs()
+	if len(addrs) == 0 {
+		t.Fatalf("backend recorded no PROXY protocol addresses (expected at least 1)")
+	}
+
+	// Every PROXY-decoded source address must be the loopback address since
+	// the test client always connects from 127.0.0.1.
+	for i, addr := range addrs {
+		host, _, err := net.SplitHostPort(addr)
+		if err != nil {
+			t.Errorf("addr[%d] %q: SplitHostPort: %v", i, addr, err)
+			continue
+		}
+		if host != "127.0.0.1" {
+			t.Errorf("addr[%d]: expected source 127.0.0.1, got %q", i, host)
+		}
+	}
+}
+
+// TestProxyProtocolListenerWrapper verifies that Caddy's
+// caddy.listeners.proxy_protocol listener wrapper can successfully parse
+// incoming PROXY protocol headers.
+//
+// The test dials Caddy's listening port directly, injects a raw PROXY v2
+// header spoofing source address 10.0.0.1:1234, then sends a normal
+// HTTP/1.1 GET request.  The Caddy server is configured to echo back the
+// remote address ({http.request.remote.host}).  The test asserts that the
+// echoed address is the spoofed 10.0.0.1.
+func TestProxyProtocolListenerWrapper(t *testing.T) {
+	tester := caddytest.NewTester(t)
+	tester.InitServer(`{
+		skip_install_trust
+		admin localhost:2999
+		http_port 9080
+		https_port 9443
+		grace_period 1ns
+		servers :9080 {
+			listener_wrappers {
+				proxy_protocol {
+					timeout 5s
+					allow 127.0.0.0/8
+				}
+			}
+		}
+	}
+	http://localhost:9080 {
+		respond "{http.request.remote.host}"
+	}`, "caddyfile")
+
+	// Dial the Caddy listener directly and inject a PROXY v2 header that
+	// claims the connection originates from 10.0.0.1:1234.
+	conn, err := net.Dial("tcp", "127.0.0.1:9080")
+	if err != nil {
+		t.Fatalf("dial: %v", err)
+	}
+	defer conn.Close()
+
+	spoofedSrc := &net.TCPAddr{IP: net.ParseIP("10.0.0.1"), Port: 1234}
+	spoofedDst := &net.TCPAddr{IP: net.ParseIP("127.0.0.1"), Port: 9080}
+	hdr := goproxy.HeaderProxyFromAddrs(2, spoofedSrc, spoofedDst)
+	if _, err := hdr.WriteTo(conn); err != nil {
+		t.Fatalf("write proxy header: %v", err)
+	}
+
+	// Write a minimal HTTP/1.1 GET request.
+	_, err = fmt.Fprintf(conn,
+		"GET / HTTP/1.1\r\nHost: localhost\r\nConnection: close\r\n\r\n")
+	if err != nil {
+		t.Fatalf("write HTTP request: %v", err)
+	}
+
+	// Read the raw response and look for the spoofed address in the body.
+	buf := make([]byte, 4096)
+	n, _ := conn.Read(buf)
+	raw := string(buf[:n])
+
+	if !strings.Contains(raw, "10.0.0.1") {
+		t.Errorf("expected spoofed address 10.0.0.1 in response body; full response:\n%s", raw)
+	}
+}
@@ -386,6 +386,68 @@ func TestReverseProxyHealthCheck(t *testing.T) {
 	tester.AssertGetResponse("http://localhost:9080/", 200, "Hello, World!")
 }

+// TestReverseProxyHealthCheckPortUsed verifies that health_port is actually
+// used for active health checks and not the upstream's main port. This is a
+// regression test for https://github.com/caddyserver/caddy/issues/7524.
+func TestReverseProxyHealthCheckPortUsed(t *testing.T) {
+	// upstream server: serves proxied requests normally, but returns 503 for
+	// /health so that if health checks mistakenly hit this port the upstream
+	// gets marked unhealthy and the proxy returns 503.
+	upstreamSrv := &http.Server{
+		Handler: http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
+			if req.URL.Path == "/health" {
+				w.WriteHeader(http.StatusServiceUnavailable)
+				return
+			}
+			_, _ = w.Write([]byte("Hello, World!"))
+		}),
+	}
+	ln0, err := net.Listen("tcp", "127.0.0.1:2022")
+	if err != nil {
+		t.Fatalf("failed to listen on 127.0.0.1:2022: %v", err)
+	}
+	go upstreamSrv.Serve(ln0)
+	t.Cleanup(func() { upstreamSrv.Close(); ln0.Close() })
+
+	// separate health check server on the configured health_port: returns 200
+	// so the upstream is marked healthy only if health checks go to this port.
+	healthSrv := &http.Server{
+		Handler: http.HandlerFunc(func(w http.ResponseWriter, req *http.Request) {
+			_, _ = w.Write([]byte("ok"))
+		}),
+	}
+	ln1, err := net.Listen("tcp", "127.0.0.1:2023")
+	if err != nil {
+		t.Fatalf("failed to listen on 127.0.0.1:2023: %v", err)
+	}
+	go healthSrv.Serve(ln1)
+	t.Cleanup(func() { healthSrv.Close(); ln1.Close() })
+
+	tester := caddytest.NewTester(t)
+	tester.InitServer(`
+	{
+		skip_install_trust
+		admin localhost:2999
+		http_port     9080
+		https_port    9443
+		grace_period 1ns
+	}
+	http://localhost:9080 {
+		reverse_proxy {
+			to localhost:2022
+
+			health_uri /health
+			health_port 2023
+			health_interval 10ms
+			health_timeout 100ms
+			health_passes 1
+			health_fails 1
+		}
+	}
+	`, "caddyfile")
+	tester.AssertGetResponse("http://localhost:9080/", 200, "Hello, World!")
+}
+
 func TestReverseProxyHealthCheckUnixSocket(t *testing.T) {
 	if runtime.GOOS == "windows" {
 		t.SkipNow()
@@ -0,0 +1,15 @@
+# Used by import_block_snippet_non_replaced_block_from_separate_file.caddyfiletest
+
+(snippet) {
+	header {
+		reverse_proxy localhost:3000
+		{block}
+	}
+}
+
+# This snippet being unused by the test Caddyfile is intentional.
+# This is to test that a panic runtime error triggered by an out-of-range slice index access
+# will not happen again, please see issue #7518 and pull request #7543 for more information
+(unused_snippet) {
+    header SomeHeader SomeValue
+}
@@ -9,9 +9,14 @@ import (
 )

 var defaultFactory = newRootCommandFactory(func() *cobra.Command {
-	return &cobra.Command{
-		Use: "caddy",
-		Long: `Caddy is an extensible server platform written in Go.
+	bin := caddy.CustomBinaryName
+	if bin == "" {
+		bin = "caddy"
+	}
+
+	long := caddy.CustomLongDescription
+	if long == "" {
+		long = `Caddy is an extensible server platform written in Go.

 At its core, Caddy merely manages configuration. Modules are plugged
 in statically at compile-time to provide useful functionality. Caddy's
@@ -91,7 +96,12 @@ package installers: https://caddyserver.com/docs/install

 Instructions for running Caddy in production are also available:
 https://caddyserver.com/docs/running
-`,
+`
+	}
+
+	return &cobra.Command{
+		Use:  bin,
+		Long: long,
 		Example: `  $ caddy run
  $ caddy run --config caddy.json
  $ caddy reload --config caddy.json
@@ -372,7 +372,7 @@ func cmdReload(fl Flags) (int, error) {
 		return caddy.ExitCodeFailedStartup, fmt.Errorf("no config file to load")
 	}

-	adminAddr, err := DetermineAdminAPIAddress(addressFlag, config, configFlag, configAdapterFlag)
+	adminAddr, err := DetermineAdminAPIAddress(addressFlag, config, configFile, configAdapterFlag)
 	if err != nil {
 		return caddy.ExitCodeFailedStartup, fmt.Errorf("couldn't determine admin API address: %v", err)
 	}
@@ -484,7 +484,13 @@ func setResourceLimits(logger *zap.Logger) func() {
 	// See https://pkg.go.dev/runtime/debug#SetMemoryLimit
 	_, _ = memlimit.SetGoMemLimitWithOpts(
 		memlimit.WithLogger(
-			slog.New(zapslog.NewHandler(logger.Core())),
+			slog.New(zapslog.NewHandler(
+				logger.Core(),
+				zapslog.WithName("memlimit"),
+				// the default enables traces at ERROR level, this disables
+				// them by setting it to a level higher than any other level
+				zapslog.AddStacktraceAt(slog.Level(127)),
+			)),
 		),
 		memlimit.WithProvider(
 			memlimit.ApplyFallback(
@@ -63,10 +63,17 @@ type Context struct {
 // modules which are loaded will be properly unloaded.
 // See standard library context package's documentation.
 func NewContext(ctx Context) (Context, context.CancelFunc) {
+	newCtx, cancelCause := NewContextWithCause(ctx)
+	return newCtx, func() { cancelCause(nil) }
+}
+
+// NewContextWithCause is like NewContext but returns a context.CancelCauseFunc.
+// EXPERIMENTAL: This API is subject to change.
+func NewContextWithCause(ctx Context) (Context, context.CancelCauseFunc) {
 	newCtx := Context{moduleInstances: make(map[string][]Module), cfg: ctx.cfg, metricsRegistry: prometheus.NewPedanticRegistry()}
-	c, cancel := context.WithCancel(ctx.Context)
-	wrappedCancel := func() {
-		cancel()
+	c, cancel := context.WithCancelCause(ctx.Context)
+	wrappedCancel := func(cause error) {
+		cancel(cause)

 		for _, f := range ctx.cleanupFuncs {
 			f()
@@ -608,6 +615,11 @@ func (ctx Context) Slogger() *slog.Logger {
 		core     zapcore.Core
 		moduleID string
 	)
+
+	// the default enables traces at ERROR level, this disables
+	// them by setting it to a level higher than any other level
+	tracesOpt := zapslog.AddStacktraceAt(slog.Level(127))
+
 	if ctx.cfg == nil {
 		// often the case in tests; just use a dev logger
 		l, err := zap.NewDevelopment()
@@ -616,16 +628,16 @@ func (ctx Context) Slogger() *slog.Logger {
 		}

 		core = l.Core()
-		handler = zapslog.NewHandler(core)
+		handler = zapslog.NewHandler(core, tracesOpt)
 	} else {
 		mod := ctx.Module()
 		if mod == nil {
 			core = Log().Core()
-			handler = zapslog.NewHandler(core)
+			handler = zapslog.NewHandler(core, tracesOpt)
 		} else {
 			moduleID = string(mod.CaddyModule().ID)
 			core = ctx.cfg.Logging.Logger(mod).Core()
-			handler = zapslog.NewHandler(core, zapslog.WithName(moduleID))
+			handler = zapslog.NewHandler(core, zapslog.WithName(moduleID), tracesOpt)
 		}
 	}

@@ -1,6 +1,6 @@
 module github.com/caddyserver/caddy/v2

-go 1.25
+go 1.25.0

 require (
 	github.com/BurntSushi/toml v1.6.0
@@ -9,7 +9,7 @@ require (
 	github.com/Masterminds/sprig/v3 v3.3.0
 	github.com/alecthomas/chroma/v2 v2.23.1
 	github.com/aryann/difflib v0.0.0-20210328193216-ff5ff6dc229b
-	github.com/caddyserver/certmagic v0.25.1
+	github.com/caddyserver/certmagic v0.25.2
 	github.com/caddyserver/zerossl v0.1.5
 	github.com/cloudflare/circl v1.6.3
 	github.com/dustin/go-humanize v1.0.1
@@ -18,10 +18,10 @@ require (
 	github.com/google/uuid v1.6.0
 	github.com/klauspost/compress v1.18.4
 	github.com/klauspost/cpuid/v2 v2.3.0
-	github.com/mholt/acmez/v3 v3.1.4
+	github.com/mholt/acmez/v3 v3.1.6
 	github.com/prometheus/client_golang v1.23.2
 	github.com/quic-go/quic-go v0.59.0
-	github.com/smallstep/certificates v0.30.0-rc2.0.20260211214201-20608299c29c
+	github.com/smallstep/certificates v0.30.0-rc3
 	github.com/smallstep/nosql v0.7.0
 	github.com/smallstep/truststore v0.13.0
 	github.com/spf13/cobra v1.10.2
@@ -35,13 +35,13 @@ require (
 	go.opentelemetry.io/contrib/propagators/autoprop v0.65.0
 	go.opentelemetry.io/otel v1.40.0
 	go.opentelemetry.io/otel/sdk v1.40.0
-	go.step.sm/crypto v0.76.0
+	go.step.sm/crypto v0.76.2
 	go.uber.org/automaxprocs v1.6.0
 	go.uber.org/zap v1.27.1
 	go.uber.org/zap/exp v0.3.0
 	golang.org/x/crypto v0.48.0
-	golang.org/x/crypto/x509roots/fallback v0.0.0-20250927194341-2beaa59a3c99
-	golang.org/x/net v0.50.0
+	golang.org/x/crypto/x509roots/fallback v0.0.0-20260213171211-a408498e5541
+	golang.org/x/net v0.51.0
 	golang.org/x/sync v0.19.0
 	golang.org/x/term v0.40.0
 	golang.org/x/time v0.14.0
@@ -108,18 +108,18 @@ require (
 	go.yaml.in/yaml/v2 v2.4.3 // indirect
 	go.yaml.in/yaml/v3 v3.0.4 // indirect
 	golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546 // indirect
-	golang.org/x/oauth2 v0.34.0 // indirect
-	google.golang.org/api v0.265.0 // indirect
+	golang.org/x/oauth2 v0.35.0 // indirect
+	google.golang.org/api v0.266.0 // indirect
 	google.golang.org/genproto/googleapis/api v0.0.0-20260128011058-8636f8732409 // indirect
-	google.golang.org/genproto/googleapis/rpc v0.0.0-20260128011058-8636f8732409 // indirect
+	google.golang.org/genproto/googleapis/rpc v0.0.0-20260203192932-546029d2fa20 // indirect
 	google.golang.org/grpc/cmd/protoc-gen-go-grpc v1.5.1 // indirect
 )

 require (
-	filippo.io/edwards25519 v1.1.0 // indirect
+	filippo.io/edwards25519 v1.2.0 // indirect
 	github.com/AndreasBriese/bbloom v0.0.0-20190825152654-46b345b51c96 // indirect
 	github.com/Masterminds/goutils v1.1.1 // indirect
-	github.com/Masterminds/semver/v3 v3.3.1 // indirect
+	github.com/Masterminds/semver/v3 v3.4.0 // indirect
 	github.com/beorn7/perks v1.0.1 // indirect
 	github.com/cespare/xxhash v1.1.0 // indirect
 	github.com/cespare/xxhash/v2 v2.3.0
@@ -145,7 +145,7 @@ require (
 	github.com/mattn/go-colorable v0.1.14 // indirect
 	github.com/mattn/go-isatty v0.0.20 // indirect
 	github.com/mgutz/ansi v0.0.0-20200706080929-d51e80ef957d // indirect
-	github.com/miekg/dns v1.1.70 // indirect
+	github.com/miekg/dns v1.1.72 // indirect
 	github.com/mitchellh/copystructure v1.2.0 // indirect
 	github.com/mitchellh/go-ps v1.0.0 // indirect
 	github.com/mitchellh/reflectwalk v1.0.2 // indirect
@@ -172,7 +172,7 @@ require (
 	golang.org/x/sys v0.41.0
 	golang.org/x/text v0.34.0
 	golang.org/x/tools v0.42.0 // indirect
-	google.golang.org/grpc v1.78.0 // indirect
+	google.golang.org/grpc v1.79.1 // indirect
 	google.golang.org/protobuf v1.36.11 // indirect
 	howett.net/plist v1.0.0 // indirect
 )
@@ -14,12 +14,14 @@ cloud.google.com/go/kms v1.25.0 h1:gVqvGGUmz0nYCmtoxWmdc1wli2L1apgP8U4fghPGSbQ=
 cloud.google.com/go/kms v1.25.0/go.mod h1:XIdHkzfj0bUO3E+LvwPg+oc7s58/Ns8Nd8Sdtljihbk=
 cloud.google.com/go/longrunning v0.8.0 h1:LiKK77J3bx5gDLi4SMViHixjD2ohlkwBi+mKA7EhfW8=
 cloud.google.com/go/longrunning v0.8.0/go.mod h1:UmErU2Onzi+fKDg2gR7dusz11Pe26aknR4kHmJJqIfk=
+code.pfad.fr/check v1.1.0 h1:GWvjdzhSEgHvEHe2uJujDcpmZoySKuHQNrZMfzfO0bE=
+code.pfad.fr/check v1.1.0/go.mod h1:NiUH13DtYsb7xp5wll0U4SXx7KhXQVCtRgdC96IPfoM=
 dario.cat/mergo v1.0.2 h1:85+piFYR1tMbRrLcDwR18y4UKJ3aH1Tbzi24VRW1TK8=
 dario.cat/mergo v1.0.2/go.mod h1:E/hbnu0NxMFBjpMIE34DRGLWqDy0g5FuKDhCb31ngxA=
 filippo.io/bigmod v0.1.0 h1:UNzDk7y9ADKST+axd9skUpBQeW7fG2KrTZyOE4uGQy8=
 filippo.io/bigmod v0.1.0/go.mod h1:OjOXDNlClLblvXdwgFFOQFJEocLhhtai8vGLy0JCZlI=
-filippo.io/edwards25519 v1.1.0 h1:FNf4tywRC1HmFuKW5xopWpigGjJKiJSV0Cqo0cJWDaA=
-filippo.io/edwards25519 v1.1.0/go.mod h1:BxyFTGdWcka3PhytdK4V28tE5sGfRvvvRV7EaN4VDT4=
+filippo.io/edwards25519 v1.2.0 h1:crnVqOiS4jqYleHd9vaKZ+HKtHfllngJIiOpNpoJsjo=
+filippo.io/edwards25519 v1.2.0/go.mod h1:xzAOLCNug/yB62zG1bQ8uziwrIqIuxhctzJT18Q77mc=
 github.com/AndreasBriese/bbloom v0.0.0-20190825152654-46b345b51c96 h1:cTp8I5+VIoKjsnZuH8vjyaysT/ses3EvZeaV/1UkF2M=
 github.com/AndreasBriese/bbloom v0.0.0-20190825152654-46b345b51c96/go.mod h1:bOvUY6CB00SOBii9/FifXqc0awNKxLFCL/+pkDPuyl8=
 github.com/BurntSushi/toml v0.3.1/go.mod h1:xHWCNGjB5oqiDr8zfno3MHue2Ht5sIBksp03qcyfWMU=
@@ -32,8 +34,8 @@ github.com/KimMachineGun/automemlimit v0.7.5 h1:RkbaC0MwhjL1ZuBKunGDjE/ggwAX43Dw
 github.com/KimMachineGun/automemlimit v0.7.5/go.mod h1:QZxpHaGOQoYvFhv/r4u3U0JTC2ZcOwbSr11UZF46UBM=
 github.com/Masterminds/goutils v1.1.1 h1:5nUrii3FMTL5diU80unEVvNevw1nH4+ZV4DSLVJLSYI=
 github.com/Masterminds/goutils v1.1.1/go.mod h1:8cTjp+g8YejhMuvIA5y2vz3BpJxksy863GQaJW2MFNU=
-github.com/Masterminds/semver/v3 v3.3.1 h1:QtNSWtVZ3nBfk8mAOu/B6v7FMJ+NHTIgUPi7rj+4nv4=
-github.com/Masterminds/semver/v3 v3.3.1/go.mod h1:4V+yj/TJE1HU9XfppCwVMZq3I84lprf4nC11bSS5beM=
+github.com/Masterminds/semver/v3 v3.4.0 h1:Zog+i5UMtVoCU8oKka5P7i9q9HgrJeGzI9SA1Xbatp0=
+github.com/Masterminds/semver/v3 v3.4.0/go.mod h1:4V+yj/TJE1HU9XfppCwVMZq3I84lprf4nC11bSS5beM=
 github.com/Masterminds/sprig/v3 v3.3.0 h1:mQh0Yrg1XPo6vjYXgtf5OtijNAKJRNcTdOOGZe3tPhs=
 github.com/Masterminds/sprig/v3 v3.3.0/go.mod h1:Zy1iXRYNqNLUolqCpL4uhk6SHUMAOSCzdgBfDb35Lz0=
 github.com/OneOfOne/xxhash v1.2.2 h1:KMrpdQIwFcEqXDklaen+P1axHaj9BSKzvpUUfnHldSE=
@@ -83,8 +85,8 @@ github.com/aws/smithy-go v1.24.0 h1:LpilSUItNPFr1eY85RYgTIg5eIEPtvFbskaFcmmIUnk=
 github.com/aws/smithy-go v1.24.0/go.mod h1:LEj2LM3rBRQJxPZTB4KuzZkaZYnZPnvgIhb4pu07mx0=
 github.com/beorn7/perks v1.0.1 h1:VlbKKnNfV8bJzeqoa4cOKqO6bYr3WgKZxO8Z16+hsOM=
 github.com/beorn7/perks v1.0.1/go.mod h1:G2ZrVWU2WbWT9wwq4/hrbKbnv/1ERSJQ0ibhJ6rlkpw=
-github.com/caddyserver/certmagic v0.25.1 h1:4sIKKbOt5pg6+sL7tEwymE1x2bj6CHr80da1CRRIPbY=
-github.com/caddyserver/certmagic v0.25.1/go.mod h1:VhyvndxtVton/Fo/wKhRoC46Rbw1fmjvQ3GjHYSQTEY=
+github.com/caddyserver/certmagic v0.25.2 h1:D7xcS7ggX/WEY54x0czj7ioTkmDWKIgxtIi2OcQclUc=
+github.com/caddyserver/certmagic v0.25.2/go.mod h1:llW/CvsNmza8S6hmsuggsZeiX+uS27dkqY27wDIuBWg=
 github.com/caddyserver/zerossl v0.1.5 h1:dkvOjBAEEtY6LIGAHei7sw2UgqSD6TrWweXpV7lvEvE=
 github.com/caddyserver/zerossl v0.1.5/go.mod h1:CxA0acn7oEGO6//4rtrRjYgEoa4MFw/XofZnrYwGqG4=
 github.com/ccoveille/go-safecast/v2 v2.0.0 h1:+5eyITXAUj3wMjad6cRVJKGnC7vDS55zk0INzJagub0=
@@ -223,6 +225,10 @@ github.com/kr/text v0.2.0 h1:5Nx0Ya0ZqY2ygV366QzturHI13Jq95ApcVaJBhpS+AY=
 github.com/kr/text v0.2.0/go.mod h1:eLer722TekiGuMkidMxC/pM04lWEeraHUUmBw8l2grE=
 github.com/kylelemons/godebug v1.1.0 h1:RPNrshWIDI6G2gRW9EHilWtl7Z6Sb1BR0xunSBf0SNc=
 github.com/kylelemons/godebug v1.1.0/go.mod h1:9/0rRGxNHcop5bhtWyNeEfOS8JIWk580+fNqagV/RAw=
+github.com/letsencrypt/challtestsrv v1.4.2 h1:0ON3ldMhZyWlfVNYYpFuWRTmZNnyfiL9Hh5YzC3JVwU=
+github.com/letsencrypt/challtestsrv v1.4.2/go.mod h1:GhqMqcSoeGpYd5zX5TgwA6er/1MbWzx/o7yuuVya+Wk=
+github.com/letsencrypt/pebble/v2 v2.10.0 h1:Wq6gYXlsY6ubqI3hhxsTzdyotvfdjFBxuwYqCLCnj/U=
+github.com/letsencrypt/pebble/v2 v2.10.0/go.mod h1:Sk8cmUIPcIdv2nINo+9PB4L+ZBhzY+F9A1a/h/xmWiQ=
 github.com/libdns/libdns v1.1.1 h1:wPrHrXILoSHKWJKGd0EiAVmiJbFShguILTg9leS/P/U=
 github.com/libdns/libdns v1.1.1/go.mod h1:4Bj9+5CQiNMVGf87wjX4CY3HQJypUHRuLvlsfsZqLWQ=
 github.com/magiconair/properties v1.8.0/go.mod h1:PppfXfuXeibc/6YijjN8zIbojt8czPbwD3XqdrwzmxQ=
@@ -234,10 +240,10 @@ github.com/mattn/go-isatty v0.0.20 h1:xfD0iDuEKnDkl03q4limB+vH+GxLEtL/jb4xVJSWWE
 github.com/mattn/go-isatty v0.0.20/go.mod h1:W+V8PltTTMOvKvAeJH7IuucS94S2C6jfK/D7dTCTo3Y=
 github.com/mgutz/ansi v0.0.0-20200706080929-d51e80ef957d h1:5PJl274Y63IEHC+7izoQE9x6ikvDFZS2mDVS3drnohI=
 github.com/mgutz/ansi v0.0.0-20200706080929-d51e80ef957d/go.mod h1:01TrycV0kFyexm33Z7vhZRXopbI8J3TDReVlkTgMUxE=
-github.com/mholt/acmez/v3 v3.1.4 h1:DyzZe/RnAzT3rpZj/2Ii5xZpiEvvYk3cQEN/RmqxwFQ=
-github.com/mholt/acmez/v3 v3.1.4/go.mod h1:L1wOU06KKvq7tswuMDwKdcHeKpFFgkppZy/y0DFxagQ=
-github.com/miekg/dns v1.1.70 h1:DZ4u2AV35VJxdD9Fo9fIWm119BsQL5cZU1cQ9s0LkqA=
-github.com/miekg/dns v1.1.70/go.mod h1:+EuEPhdHOsfk6Wk5TT2CzssZdqkmFhf8r+aVyDEToIs=
+github.com/mholt/acmez/v3 v3.1.6 h1:eGVQNObP0pBN4sxqrXeg7MYqTOWyoiYpQqITVWlrevk=
+github.com/mholt/acmez/v3 v3.1.6/go.mod h1:5nTPosTGosLxF3+LU4ygbgMRFDhbAVpqMI4+a4aHLBY=
+github.com/miekg/dns v1.1.72 h1:vhmr+TF2A3tuoGNkLDFK9zi36F2LS+hKTRW0Uf8kbzI=
+github.com/miekg/dns v1.1.72/go.mod h1:+EuEPhdHOsfk6Wk5TT2CzssZdqkmFhf8r+aVyDEToIs=
 github.com/mitchellh/copystructure v1.2.0 h1:vpKXTN4ewci03Vljg/q9QvCGUDttBOGBIa15WveJJGw=
 github.com/mitchellh/copystructure v1.2.0/go.mod h1:qLl+cE2AmVv+CoeAwDPye/v+N2HKCj9FbZEVFJRxO9s=
 github.com/mitchellh/go-homedir v1.1.0/go.mod h1:SfyaCUpYCn1Vlf4IUYiD9fPX4A5wJrkLzIz1N1q0pr0=
@@ -295,8 +301,8 @@ github.com/slackhq/nebula v1.10.3 h1:EstYj8ODEcv6T0R9X5BVq1zgWZnyU5gtPzk99QF1PMU
 github.com/slackhq/nebula v1.10.3/go.mod h1:IL5TUQm4x9IFx2kCKPYm1gP47pwd5b8QGnnBH2RHnvs=
 github.com/smallstep/assert v0.0.0-20200723003110-82e2b9b3b262 h1:unQFBIznI+VYD1/1fApl1A+9VcBk+9dcqGfnePY87LY=
 github.com/smallstep/assert v0.0.0-20200723003110-82e2b9b3b262/go.mod h1:MyOHs9Po2fbM1LHej6sBUT8ozbxmMOFG+E+rx/GSGuc=
-github.com/smallstep/certificates v0.30.0-rc2.0.20260211214201-20608299c29c h1:XQpX0IPYUAoJ661YlgfOJmY48ZOhIbglw4E2gw9mcyc=
-github.com/smallstep/certificates v0.30.0-rc2.0.20260211214201-20608299c29c/go.mod h1:75NRLmYJq6ZcCb8ApJc+W1eL4oMYwjeufMJDHpv4rx4=
+github.com/smallstep/certificates v0.30.0-rc3 h1:Lx/NNJ4n+L3Pyx5NtVRGXeqviPPXTFFGLRiC1fCwU50=
+github.com/smallstep/certificates v0.30.0-rc3/go.mod h1:e5/ylYYpvnjCVZz6RpyOkpTe73EGPYoL+8TZZ5EtLjI=
 github.com/smallstep/cli-utils v0.12.2 h1:lGzM9PJrH/qawbzMC/s2SvgLdJPKDWKwKzx9doCVO+k=
 github.com/smallstep/cli-utils v0.12.2/go.mod h1:uCPqefO29goHLGqFnwk0i8W7XJu18X3WHQFRtOm/00Y=
 github.com/smallstep/go-attestation v0.4.4-0.20241119153605-2306d5b464ca h1:VX8L0r8vybH0bPeaIxh4NQzafKQiqvlOn8pmOXbFLO4=
@@ -425,8 +431,8 @@ go.opentelemetry.io/otel/trace v1.40.0 h1:WA4etStDttCSYuhwvEa8OP8I5EWu24lkOzp+ZY
 go.opentelemetry.io/otel/trace v1.40.0/go.mod h1:zeAhriXecNGP/s2SEG3+Y8X9ujcJOTqQ5RgdEJcawiA=
 go.opentelemetry.io/proto/otlp v1.9.0 h1:l706jCMITVouPOqEnii2fIAuO3IVGBRPV5ICjceRb/A=
 go.opentelemetry.io/proto/otlp v1.9.0/go.mod h1:xE+Cx5E/eEHw+ISFkwPLwCZefwVjY+pqKg1qcK03+/4=
-go.step.sm/crypto v0.76.0 h1:K23BSaeoiY7Y5dvvijTeYC9EduDBetNwQYMBwMhi1aA=
-go.step.sm/crypto v0.76.0/go.mod h1:PXYJdKkK8s+GHLwLguFaLxHNAFsFL3tL1vSBrYfey5k=
+go.step.sm/crypto v0.76.2 h1:JJ/yMcs/rmcCAwlo+afrHjq74XBFRTJw5B2y4Q4Z4c4=
+go.step.sm/crypto v0.76.2/go.mod h1:m6KlB/HzIuGFep0UWI5e0SYi38UxpoKeCg6qUaHV6/Q=
 go.uber.org/automaxprocs v1.6.0 h1:O3y2/QNTOdbF+e/dpXNNW7Rx2hZ4sTIPyybbxyNqTUs=
 go.uber.org/automaxprocs v1.6.0/go.mod h1:ifeIMSnPZuznNm6jmdzmU3/bfk01Fe2fotchwEFJ8r8=
 go.uber.org/goleak v1.3.0 h1:2K3zAYmnTNqV73imy9J1T3WC+gmCePx2hEGkimedGto=
@@ -452,8 +458,8 @@ golang.org/x/crypto v0.23.0/go.mod h1:CKFgDieR+mRhux2Lsu27y0fO304Db0wZe70UKqHu0v
 golang.org/x/crypto v0.33.0/go.mod h1:bVdXmD7IV/4GdElGPozy6U7lWdRXA4qyRVGJV57uQ5M=
 golang.org/x/crypto v0.48.0 h1:/VRzVqiRSggnhY7gNRxPauEQ5Drw9haKdM0jqfcCFts=
 golang.org/x/crypto v0.48.0/go.mod h1:r0kV5h3qnFPlQnBSrULhlsRfryS2pmewsg+XfMgkVos=
-golang.org/x/crypto/x509roots/fallback v0.0.0-20250927194341-2beaa59a3c99 h1:CH0o4/bZX6KIUCjjgjmtNtfM/kXSkTYlzTOB9vZF45g=
-golang.org/x/crypto/x509roots/fallback v0.0.0-20250927194341-2beaa59a3c99/go.mod h1:MEIPiCnxvQEjA4astfaKItNwEVZA5Ki+3+nyGbJ5N18=
+golang.org/x/crypto/x509roots/fallback v0.0.0-20260213171211-a408498e5541 h1:FmKxj9ocLKn45jiR2jQMwCVhDvaK7fKQFzfuT9GvyK8=
+golang.org/x/crypto/x509roots/fallback v0.0.0-20260213171211-a408498e5541/go.mod h1:+UoQFNBq2p2wO+Q6ddVtYc25GZ6VNdOMyyrd4nrqrKs=
 golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546 h1:mgKeJMpvi0yx/sU5GsxQ7p6s2wtOnGAHZWCHUM4KGzY=
 golang.org/x/exp v0.0.0-20251023183803-a4bb9ffd2546/go.mod h1:j/pmGrbnkbPtQfxEe5D0VQhZC6qKbfKifgD0oM7sR70=
 golang.org/x/mod v0.6.0-dev.0.20220419223038-86c51ed26bb4/go.mod h1:jJ57K6gSWd91VN4djpZkiMVwK6gcyfeH4XE8wZrZaV4=
@@ -471,10 +477,10 @@ golang.org/x/net v0.10.0/go.mod h1:0qNGK6F8kojg2nk9dLZ2mShWaEBan6FAoqfSigmmuDg=
 golang.org/x/net v0.15.0/go.mod h1:idbUs1IY1+zTqbi8yxTbhexhEEk5ur9LInksu6HrEpk=
 golang.org/x/net v0.21.0/go.mod h1:bIjVDfnllIU7BJ2DNgfnXvpSvtn8VRwhlsaeUTyUS44=
 golang.org/x/net v0.25.0/go.mod h1:JkAGAh7GEvH74S6FOH42FLoXpXbE/aqXSrIQjXgsiwM=
-golang.org/x/net v0.50.0 h1:ucWh9eiCGyDR3vtzso0WMQinm2Dnt8cFMuQa9K33J60=
-golang.org/x/net v0.50.0/go.mod h1:UgoSli3F/pBgdJBHCTc+tp3gmrU4XswgGRgtnwWTfyM=
-golang.org/x/oauth2 v0.34.0 h1:hqK/t4AKgbqWkdkcAeI8XLmbK+4m4G5YeQRrmiotGlw=
-golang.org/x/oauth2 v0.34.0/go.mod h1:lzm5WQJQwKZ3nwavOZ3IS5Aulzxi68dUSgRHujetwEA=
+golang.org/x/net v0.51.0 h1:94R/GTO7mt3/4wIKpcR5gkGmRLOuE/2hNGeWq/GBIFo=
+golang.org/x/net v0.51.0/go.mod h1:aamm+2QF5ogm02fjy5Bb7CQ0WMt1/WVM7FtyaTLlA9Y=
+golang.org/x/oauth2 v0.35.0 h1:Mv2mzuHuZuY2+bkyWXIHMfhNdJAdwW3FuWeCPYN5GVQ=
+golang.org/x/oauth2 v0.35.0/go.mod h1:lzm5WQJQwKZ3nwavOZ3IS5Aulzxi68dUSgRHujetwEA=
 golang.org/x/sync v0.0.0-20190423024810-112230192c58/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sync v0.0.0-20220722155255-886fb9371eb4/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
 golang.org/x/sync v0.1.0/go.mod h1:RxMgew5VJxzue5/jJTE5uejpjVlOe/izrB70Jof72aM=
@@ -537,16 +543,16 @@ golang.org/x/tools v0.42.0/go.mod h1:Ma6lCIwGZvHK6XtgbswSoWroEkhugApmsXyrUmBhfr0
 golang.org/x/xerrors v0.0.0-20190717185122-a985d3407aa7/go.mod h1:I/5z698sn9Ka8TeJc9MKroUUfqBBauWjQqLJ2OPfmY0=
 gonum.org/v1/gonum v0.16.0 h1:5+ul4Swaf3ESvrOnidPp4GZbzf0mxVQpDCYUQE7OJfk=
 gonum.org/v1/gonum v0.16.0/go.mod h1:fef3am4MQ93R2HHpKnLk4/Tbh/s0+wqD5nfa6Pnwy4E=
-google.golang.org/api v0.265.0 h1:FZvfUdI8nfmuNrE34aOWFPmLC+qRBEiNm3JdivTvAAU=
-google.golang.org/api v0.265.0/go.mod h1:uAvfEl3SLUj/7n6k+lJutcswVojHPp2Sp08jWCu8hLY=
+google.golang.org/api v0.266.0 h1:hco+oNCf9y7DmLeAtHJi/uBAY7n/7XC9mZPxu1ROiyk=
+google.golang.org/api v0.266.0/go.mod h1:Jzc0+ZfLnyvXma3UtaTl023TdhZu6OMBP9tJ+0EmFD0=
 google.golang.org/genproto v0.0.0-20260128011058-8636f8732409 h1:VQZ/yAbAtjkHgH80teYd2em3xtIkkHd7ZhqfH2N9CsM=
 google.golang.org/genproto v0.0.0-20260128011058-8636f8732409/go.mod h1:rxKD3IEILWEu3P44seeNOAwZN4SaoKaQ/2eTg4mM6EM=
 google.golang.org/genproto/googleapis/api v0.0.0-20260128011058-8636f8732409 h1:merA0rdPeUV3YIIfHHcH4qBkiQAc1nfCKSI7lB4cV2M=
 google.golang.org/genproto/googleapis/api v0.0.0-20260128011058-8636f8732409/go.mod h1:fl8J1IvUjCilwZzQowmw2b7HQB2eAuYBabMXzWurF+I=
-google.golang.org/genproto/googleapis/rpc v0.0.0-20260128011058-8636f8732409 h1:H86B94AW+VfJWDqFeEbBPhEtHzJwJfTbgE2lZa54ZAQ=
-google.golang.org/genproto/googleapis/rpc v0.0.0-20260128011058-8636f8732409/go.mod h1:j9x/tPzZkyxcgEFkiKEEGxfvyumM01BEtsW8xzOahRQ=
-google.golang.org/grpc v1.78.0 h1:K1XZG/yGDJnzMdd/uZHAkVqJE+xIDOcmdSFZkBUicNc=
-google.golang.org/grpc v1.78.0/go.mod h1:I47qjTo4OKbMkjA/aOOwxDIiPSBofUtQUI5EfpWvW7U=
+google.golang.org/genproto/googleapis/rpc v0.0.0-20260203192932-546029d2fa20 h1:Jr5R2J6F6qWyzINc+4AM8t5pfUz6beZpHp678GNrMbE=
+google.golang.org/genproto/googleapis/rpc v0.0.0-20260203192932-546029d2fa20/go.mod h1:j9x/tPzZkyxcgEFkiKEEGxfvyumM01BEtsW8xzOahRQ=
+google.golang.org/grpc v1.79.1 h1:zGhSi45ODB9/p3VAawt9a+O/MULLl9dpizzNNpq7flY=
+google.golang.org/grpc v1.79.1/go.mod h1:KmT0Kjez+0dde/v2j9vzwoAScgEPx/Bw1CYChhHLrHQ=
 google.golang.org/grpc/cmd/protoc-gen-go-grpc v1.5.1 h1:F29+wU6Ee6qgu9TddPgooOdaqsxTMunOoj8KA5yuS5A=
 google.golang.org/grpc/cmd/protoc-gen-go-grpc v1.5.1/go.mod h1:5KF+wpkbTSbGcR9zteSqZV6fqFOWBl4Yde8En8MryZA=
 google.golang.org/protobuf v1.36.11 h1:fV6ZwhNocDyBLK0dj+fg8ektcVegBBuEolpbTQyBNVE=
@@ -38,10 +38,6 @@ import (
 	"github.com/caddyserver/caddy/v2/internal"
 )

-// listenFdsStart is the first file descriptor number for systemd socket activation.
-// File descriptors 0, 1, 2 are reserved for stdin, stdout, stderr.
-const listenFdsStart = 3
-
 // NetworkAddress represents one or more network addresses.
 // It contains the individual components for a parsed network
 // address of the form accepted by ParseNetworkAddress().
@@ -233,7 +229,7 @@ func (na NetworkAddress) JoinHostPort(offset uint) string {
 func (na NetworkAddress) Expand() []NetworkAddress {
 	size := na.PortRangeSize()
 	addrs := make([]NetworkAddress, size)
-	for portOffset := uint(0); portOffset < size; portOffset++ {
+	for portOffset := range size {
 		addrs[portOffset] = na.At(portOffset)
 	}
 	return addrs
@@ -309,64 +305,6 @@ func IsFdNetwork(netw string) bool {
 	return strings.HasPrefix(netw, "fd")
 }

-// getFdByName returns the file descriptor number for the given
-// socket name from systemd's LISTEN_FDNAMES environment variable.
-// Socket names are provided by systemd via socket activation.
-//
-// The name can optionally include an index to handle multiple sockets
-// with the same name: "web:0" for first, "web:1" for second, etc.
-// If no index is specified, defaults to index 0 (first occurrence).
-func getFdByName(nameWithIndex string) (int, error) {
-	if nameWithIndex == "" {
-		return 0, fmt.Errorf("socket name cannot be empty")
-	}
-
-	fdNamesStr := os.Getenv("LISTEN_FDNAMES")
-	if fdNamesStr == "" {
-		return 0, fmt.Errorf("LISTEN_FDNAMES environment variable not set")
-	}
-
-	// Parse name and optional index
-	parts := strings.Split(nameWithIndex, ":")
-	if len(parts) > 2 {
-		return 0, fmt.Errorf("invalid socket name format '%s': too many colons", nameWithIndex)
-	}
-
-	name := parts[0]
-	targetIndex := 0
-
-	if len(parts) > 1 {
-		var err error
-		targetIndex, err = strconv.Atoi(parts[1])
-		if err != nil {
-			return 0, fmt.Errorf("invalid socket index '%s': %v", parts[1], err)
-		}
-		if targetIndex < 0 {
-			return 0, fmt.Errorf("socket index cannot be negative: %d", targetIndex)
-		}
-	}
-
-	// Parse the socket names
-	names := strings.Split(fdNamesStr, ":")
-
-	// Find the Nth occurrence of the requested name
-	matchCount := 0
-	for i, fdName := range names {
-		if fdName == name {
-			if matchCount == targetIndex {
-				return listenFdsStart + i, nil
-			}
-			matchCount++
-		}
-	}
-
-	if matchCount == 0 {
-		return 0, fmt.Errorf("socket name '%s' not found in LISTEN_FDNAMES", name)
-	}
-
-	return 0, fmt.Errorf("socket name '%s' found %d times, but index %d requested", name, matchCount, targetIndex)
-}
-
 // ParseNetworkAddress parses addr into its individual
 // components. The input string is expected to be of
 // the form "network/host:port-range" where any part is
@@ -398,27 +336,9 @@ func ParseNetworkAddressWithDefaults(addr, defaultNetwork string, defaultPort ui
 		}, err
 	}
 	if IsFdNetwork(network) {
-		fdAddr := host
-
-		// Handle named socket activation (fdname/name, fdgramname/name)
-		if strings.HasPrefix(network, "fdname") || strings.HasPrefix(network, "fdgramname") {
-			fdNum, err := getFdByName(host)
-			if err != nil {
-				return NetworkAddress{}, fmt.Errorf("named socket activation: %v", err)
-			}
-			fdAddr = strconv.Itoa(fdNum)
-
-			// Normalize network to standard fd/fdgram
-			if strings.HasPrefix(network, "fdname") {
-				network = "fd"
-			} else {
-				network = "fdgram"
-			}
-		}
-
 		return NetworkAddress{
 			Network: network,
-			Host:    fdAddr,
+			Host:    host,
 		}, nil
 	}
 	var start, end uint64
@@ -592,7 +512,7 @@ func ListenerUsage(network, addr string) int {
 // contextAndCancelFunc groups context and its cancelFunc
 type contextAndCancelFunc struct {
 	context.Context
-	context.CancelFunc
+	context.CancelCauseFunc
 }

 // sharedQUICState manages GetConfigForClient
@@ -622,17 +542,17 @@ func (sqs *sharedQUICState) getConfigForClient(ch *tls.ClientHelloInfo) (*tls.Co

 // addState adds tls.Config and activeRequests to the map if not present and returns the corresponding context and its cancelFunc
 // so that when cancelled, the active tls.Config will change
-func (sqs *sharedQUICState) addState(tlsConfig *tls.Config) (context.Context, context.CancelFunc) {
+func (sqs *sharedQUICState) addState(tlsConfig *tls.Config) (context.Context, context.CancelCauseFunc) {
 	sqs.rmu.Lock()
 	defer sqs.rmu.Unlock()

 	if cacc, ok := sqs.tlsConfs[tlsConfig]; ok {
-		return cacc.Context, cacc.CancelFunc
+		return cacc.Context, cacc.CancelCauseFunc
 	}

-	ctx, cancel := context.WithCancel(context.Background())
-	wrappedCancel := func() {
-		cancel()
+	ctx, cancel := context.WithCancelCause(context.Background())
+	wrappedCancel := func(cause error) {
+		cancel(cause)

 		sqs.rmu.Lock()
 		defer sqs.rmu.Unlock()
@@ -688,13 +608,13 @@ func fakeClosedErr(l interface{ Addr() net.Addr }) error {
 // indicating that it is pretending to be closed so that the
 // server using it can terminate, while the underlying
 // socket is actually left open.
-var errFakeClosed = fmt.Errorf("listener 'closed' 😉")
+var errFakeClosed = fmt.Errorf("QUIC listener 'closed' 😉")

 type fakeCloseQuicListener struct {
 	closed              int32 // accessed atomically; belongs to this struct only
 	*sharedQuicListener       // embedded, so we also become a quic.EarlyListener
 	context             context.Context
-	contextCancel       context.CancelFunc
+	contextCancel       context.CancelCauseFunc
 }

 // Currently Accept ignores the passed context, however a situation where
@@ -717,7 +637,7 @@ func (fcql *fakeCloseQuicListener) Accept(_ context.Context) (*quic.Conn, error)

 func (fcql *fakeCloseQuicListener) Close() error {
 	if atomic.CompareAndSwapInt32(&fcql.closed, 0, 1) {
-		fcql.contextCancel()
+		fcql.contextCancel(errFakeClosed)
 	} else if atomic.CompareAndSwapInt32(&fcql.closed, 1, 2) {
 		_, _ = listenerPool.Delete(fcql.sharedQuicListener.key)
 	}
@@ -15,7 +15,6 @@
 package caddy

 import (
-	"os"
 	"reflect"
 	"testing"

@@ -653,286 +652,3 @@ func TestSplitUnixSocketPermissionsBits(t *testing.T) {
 		}
 	}
 }
-
-// TestGetFdByName tests the getFdByName function for systemd socket activation.
-func TestGetFdByName(t *testing.T) {
-	// Save original environment
-	originalFdNames := os.Getenv("LISTEN_FDNAMES")
-
-	// Restore environment after test
-	defer func() {
-		if originalFdNames != "" {
-			os.Setenv("LISTEN_FDNAMES", originalFdNames)
-		} else {
-			os.Unsetenv("LISTEN_FDNAMES")
-		}
-	}()
-
-	tests := []struct {
-		name        string
-		fdNames     string
-		socketName  string
-		expectedFd  int
-		expectError bool
-	}{
-		{
-			name:       "simple http socket",
-			fdNames:    "http",
-			socketName: "http",
-			expectedFd: 3,
-		},
-		{
-			name:       "multiple different sockets - first",
-			fdNames:    "http:https:dns",
-			socketName: "http",
-			expectedFd: 3,
-		},
-		{
-			name:       "multiple different sockets - second",
-			fdNames:    "http:https:dns",
-			socketName: "https",
-			expectedFd: 4,
-		},
-		{
-			name:       "multiple different sockets - third",
-			fdNames:    "http:https:dns",
-			socketName: "dns",
-			expectedFd: 5,
-		},
-		{
-			name:       "duplicate names - first occurrence (no index)",
-			fdNames:    "web:web:api",
-			socketName: "web",
-			expectedFd: 3,
-		},
-		{
-			name:       "duplicate names - first occurrence (explicit index 0)",
-			fdNames:    "web:web:api",
-			socketName: "web:0",
-			expectedFd: 3,
-		},
-		{
-			name:       "duplicate names - second occurrence (index 1)",
-			fdNames:    "web:web:api",
-			socketName: "web:1",
-			expectedFd: 4,
-		},
-		{
-			name:       "complex duplicates - first api",
-			fdNames:    "web:api:web:api:dns",
-			socketName: "api:0",
-			expectedFd: 4,
-		},
-		{
-			name:       "complex duplicates - second api",
-			fdNames:    "web:api:web:api:dns",
-			socketName: "api:1",
-			expectedFd: 6,
-		},
-		{
-			name:       "complex duplicates - first web",
-			fdNames:    "web:api:web:api:dns",
-			socketName: "web:0",
-			expectedFd: 3,
-		},
-		{
-			name:       "complex duplicates - second web",
-			fdNames:    "web:api:web:api:dns",
-			socketName: "web:1",
-			expectedFd: 5,
-		},
-		{
-			name:        "socket not found",
-			fdNames:     "http:https",
-			socketName:  "missing",
-			expectError: true,
-		},
-		{
-			name:        "empty socket name",
-			fdNames:     "http",
-			socketName:  "",
-			expectError: true,
-		},
-		{
-			name:        "missing LISTEN_FDNAMES",
-			fdNames:     "",
-			socketName:  "http",
-			expectError: true,
-		},
-		{
-			name:        "index out of range",
-			fdNames:     "web:web",
-			socketName:  "web:2",
-			expectError: true,
-		},
-		{
-			name:        "negative index",
-			fdNames:     "web",
-			socketName:  "web:-1",
-			expectError: true,
-		},
-		{
-			name:        "invalid index format",
-			fdNames:     "web",
-			socketName:  "web:abc",
-			expectError: true,
-		},
-		{
-			name:        "too many colons",
-			fdNames:     "web",
-			socketName:  "web:0:extra",
-			expectError: true,
-		},
-	}
-
-	for _, tc := range tests {
-		t.Run(tc.name, func(t *testing.T) {
-			// Set up environment
-			if tc.fdNames != "" {
-				os.Setenv("LISTEN_FDNAMES", tc.fdNames)
-			} else {
-				os.Unsetenv("LISTEN_FDNAMES")
-			}
-
-			// Test the function
-			fd, err := getFdByName(tc.socketName)
-
-			if tc.expectError {
-				if err == nil {
-					t.Errorf("Expected error but got none")
-				}
-			} else {
-				if err != nil {
-					t.Errorf("Expected no error but got: %v", err)
-				}
-				if fd != tc.expectedFd {
-					t.Errorf("Expected FD %d but got %d", tc.expectedFd, fd)
-				}
-			}
-		})
-	}
-}
-
-// TestParseNetworkAddressFdName tests parsing of fdname and fdgramname addresses.
-func TestParseNetworkAddressFdName(t *testing.T) {
-	// Save and restore environment
-	originalFdNames := os.Getenv("LISTEN_FDNAMES")
-	defer func() {
-		if originalFdNames != "" {
-			os.Setenv("LISTEN_FDNAMES", originalFdNames)
-		} else {
-			os.Unsetenv("LISTEN_FDNAMES")
-		}
-	}()
-
-	// Set up test environment
-	os.Setenv("LISTEN_FDNAMES", "http:https:dns")
-
-	tests := []struct {
-		input      string
-		expectAddr NetworkAddress
-		expectErr  bool
-	}{
-		{
-			input: "fdname/http",
-			expectAddr: NetworkAddress{
-				Network: "fd",
-				Host:    "3",
-			},
-		},
-		{
-			input: "fdname/https",
-			expectAddr: NetworkAddress{
-				Network: "fd",
-				Host:    "4",
-			},
-		},
-		{
-			input: "fdname/dns",
-			expectAddr: NetworkAddress{
-				Network: "fd",
-				Host:    "5",
-			},
-		},
-		{
-			input: "fdname/http:0",
-			expectAddr: NetworkAddress{
-				Network: "fd",
-				Host:    "3",
-			},
-		},
-		{
-			input: "fdname/https:0",
-			expectAddr: NetworkAddress{
-				Network: "fd",
-				Host:    "4",
-			},
-		},
-		{
-			input: "fdgramname/http",
-			expectAddr: NetworkAddress{
-				Network: "fdgram",
-				Host:    "3",
-			},
-		},
-		{
-			input: "fdgramname/https",
-			expectAddr: NetworkAddress{
-				Network: "fdgram",
-				Host:    "4",
-			},
-		},
-		{
-			input: "fdgramname/http:0",
-			expectAddr: NetworkAddress{
-				Network: "fdgram",
-				Host:    "3",
-			},
-		},
-		{
-			input:     "fdname/nonexistent",
-			expectErr: true,
-		},
-		{
-			input:     "fdgramname/nonexistent",
-			expectErr: true,
-		},
-		{
-			input:     "fdname/http:99",
-			expectErr: true,
-		},
-		{
-			input:     "fdname/invalid:abc",
-			expectErr: true,
-		},
-		// Test that old fd/N syntax still works
-		{
-			input: "fd/7",
-			expectAddr: NetworkAddress{
-				Network: "fd",
-				Host:    "7",
-			},
-		},
-		{
-			input: "fdgram/8",
-			expectAddr: NetworkAddress{
-				Network: "fdgram",
-				Host:    "8",
-			},
-		},
-	}
-
-	for i, tc := range tests {
-		actualAddr, err := ParseNetworkAddress(tc.input)
-
-		if tc.expectErr && err == nil {
-			t.Errorf("Test %d (%s): Expected error but got none", i, tc.input)
-		}
-		if !tc.expectErr && err != nil {
-			t.Errorf("Test %d (%s): Expected no error but got: %v", i, tc.input, err)
-		}
-		if !tc.expectErr && !reflect.DeepEqual(tc.expectAddr, actualAddr) {
-			t.Errorf("Test %d (%s): Expected %+v but got %+v", i, tc.input, tc.expectAddr, actualAddr)
-		}
-	}
-}
@@ -18,6 +18,7 @@ import (
 	"cmp"
 	"context"
 	"crypto/tls"
+	"errors"
 	"fmt"
 	"maps"
 	"net"
@@ -711,9 +712,10 @@ func (app *App) Stop() error {
 	// enforce grace period if configured
 	if app.GracePeriod > 0 {
 		var cancel context.CancelFunc
-		ctx, cancel = context.WithTimeout(ctx, time.Duration(app.GracePeriod))
+		timeout := time.Duration(app.GracePeriod)
+		ctx, cancel = context.WithTimeoutCause(ctx, timeout, fmt.Errorf("server graceful shutdown %ds timeout", int(timeout.Seconds())))
 		defer cancel()
-		app.logger.Info("servers shutting down; grace period initiated", zap.Duration("duration", time.Duration(app.GracePeriod)))
+		app.logger.Info("servers shutting down; grace period initiated", zap.Duration("duration", timeout))
 	} else {
 		app.logger.Info("servers shutting down with eternal grace period")
 	}
@@ -739,6 +741,9 @@ func (app *App) Stop() error {
 		}

 		if err := server.server.Shutdown(ctx); err != nil {
+			if cause := context.Cause(ctx); cause != nil && errors.Is(err, context.DeadlineExceeded) {
+				err = cause
+			}
 			app.logger.Error("server shutdown",
 				zap.Error(err),
 				zap.Strings("addresses", server.Listen))
@@ -762,6 +767,9 @@ func (app *App) Stop() error {
 		}

 		if err := server.h3server.Shutdown(ctx); err != nil {
+			if cause := context.Cause(ctx); cause != nil && errors.Is(err, context.DeadlineExceeded) {
+				err = cause
+			}
 			app.logger.Error("HTTP/3 server shutdown",
 				zap.Error(err),
 				zap.Strings("addresses", server.Listen))
@@ -424,6 +424,40 @@ redirServersLoop:
 		// we'll create a new server for all the listener addresses
 		// that are unused and serve the remaining redirects from it

+		// Sort redirect routes by host specificity to ensure exact matches
+		// take precedence over wildcards, preventing ambiguous routing.
+		slices.SortFunc(routes, func(a, b Route) int {
+			hostA := getFirstHostFromRoute(a)
+			hostB := getFirstHostFromRoute(b)
+
+			// Catch-all routes (empty host) have the lowest priority
+			if hostA == "" && hostB != "" {
+				return 1
+			}
+			if hostB == "" && hostA != "" {
+				return -1
+			}
+
+			hasWildcardA := strings.Contains(hostA, "*")
+			hasWildcardB := strings.Contains(hostB, "*")
+
+			// Exact domains take precedence over wildcards
+			if !hasWildcardA && hasWildcardB {
+				return -1
+			}
+			if hasWildcardA && !hasWildcardB {
+				return 1
+			}
+
+			// If both are exact or both are wildcards, the longer one is more specific
+			if len(hostA) != len(hostB) {
+				return len(hostB) - len(hostA)
+			}
+
+			// Tie-breaker: alphabetical order to ensure determinism
+			return strings.Compare(hostA, hostB)
+		})
+
 		// Use the sorted srvNames to consistently find the target server
 		for _, srvName := range srvNames {
 			srv := app.Servers[srvName]
@@ -580,6 +614,27 @@ func (app *App) createAutomationPolicies(ctx caddy.Context, internalNames, tails
 		}
 	}

+	// Ensure automation policies' CertMagic configs are rebuilt when
+	// ACME issuer templates may have been modified above (for example,
+	// alternate ports filled in by the HTTP app). If a policy is already
+	// provisioned, perform a lightweight rebuild of the CertMagic config
+	// so issuers receive SetConfig with the updated templates; otherwise
+	// run a normal Provision to initialize the policy.
+	for i, ap := range app.tlsApp.Automation.Policies {
+		// If the policy is already provisioned, rebuild only the CertMagic
+		// config so issuers get SetConfig with updated templates. Otherwise
+		// provision the policy normally (which may load modules).
+		if ap.IsProvisioned() {
+			if err := ap.RebuildCertMagic(app.tlsApp); err != nil {
+				return fmt.Errorf("rebuilding certmagic config for automation policy %d: %v", i, err)
+			}
+		} else {
+			if err := ap.Provision(app.tlsApp); err != nil {
+				return fmt.Errorf("provisioning automation policy %d after auto-HTTPS defaults: %v", i, err)
+			}
+		}
+	}
+
 	if basePolicy == nil {
 		// no base policy found; we will make one
 		basePolicy = new(caddytls.AutomationPolicy)
@@ -793,3 +848,26 @@ func isTailscaleDomain(name string) bool {
 }

 type acmeCapable interface{ GetACMEIssuer() *caddytls.ACMEIssuer }
+
+// getFirstHostFromRoute traverses a route's matchers to find the Host rule.
+// Since we are dealing with internally generated redirect routes, the host
+// is typically the first string within the MatchHost.
+func getFirstHostFromRoute(r Route) string {
+	for _, matcherSet := range r.MatcherSets {
+		for _, m := range matcherSet {
+			// Check if the matcher is of type MatchHost (value or pointer)
+			switch hm := m.(type) {
+			case MatchHost:
+				if len(hm) > 0 {
+					return hm[0]
+				}
+			case *MatchHost:
+				if len(*hm) > 0 {
+					return (*hm)[0]
+				}
+			}
+		}
+	}
+	// Return an empty string if it's a catch-all route (no specific host)
+	return ""
+}
@@ -307,14 +307,6 @@ func (rw *responseWriter) FlushError() error {
 	return http.NewResponseController(rw.ResponseWriter).Flush()
 }

-// Flush calls FlushError() and simply discards any error. It is only implemented for backwards
-// compatibility with legacy code that does not use FlushError; we know at least one sponsor
-// needs this. It should not be relied upon as a stable part of the exported API, as it may be
-// removed in the future.
-func (rw *responseWriter) Flush() {
-	_ = rw.FlushError()
-}
-
 // Write writes to the response. If the response qualifies,
 // it is encoded using the encoder, which is initialized
 // if not done so already.
@@ -720,6 +720,7 @@ var globSafeRepl = strings.NewReplacer(
 	"*", "\\*",
 	"[", "\\[",
 	"?", "\\?",
+	"\\", "\\\\",
 )

 const (
@@ -20,7 +20,9 @@ import (
 	"net/http/httptest"
 	"net/url"
 	"os"
+	"path/filepath"
 	"runtime"
+	"strings"
 	"testing"

 	"github.com/caddyserver/caddy/v2"
@@ -28,6 +30,13 @@ import (
 	"github.com/caddyserver/caddy/v2/modules/caddyhttp"
 )

+type testCase struct {
+	path         string
+	expectedPath string
+	expectedType string
+	matched      bool
+}
+
 func TestFileMatcher(t *testing.T) {
 	// Windows doesn't like colons in files names
 	isWindows := runtime.GOOS == "windows"
@@ -45,12 +54,7 @@ func TestFileMatcher(t *testing.T) {
 		f.Close()
 	}

-	for i, tc := range []struct {
-		path         string
-		expectedPath string
-		expectedType string
-		matched      bool
-	}{
+	for i, tc := range []testCase{
 		{
 			path:         "/foo.txt",
 			expectedPath: "/foo.txt",
@@ -116,44 +120,71 @@ func TestFileMatcher(t *testing.T) {
 			matched:      !isWindows,
 		},
 	} {
-		m := &MatchFile{
-			fsmap:    &filesystems.FileSystemMap{},
-			Root:     "./testdata",
-			TryFiles: []string{"{http.request.uri.path}", "{http.request.uri.path}/"},
-		}
+		fileMatcherTest(t, i, tc)
+	}
+}

-		u, err := url.Parse(tc.path)
-		if err != nil {
-			t.Errorf("Test %d: parsing path: %v", i, err)
-		}
+func TestFileMatcherNonWindows(t *testing.T) {
+	if runtime.GOOS == "windows" {
+		return
+	}

-		req := &http.Request{URL: u}
-		repl := caddyhttp.NewTestReplacer(req)
+	// this is impossible to test on Windows, but tests a security patch for other platforms
+	tc := testCase{
+		path:         "/foodir/secr%5Cet.txt",
+		expectedPath: "/foodir/secr\\et.txt",
+		expectedType: "file",
+		matched:      true,
+	}

-		result, err := m.MatchWithError(req)
-		if err != nil {
-			t.Errorf("Test %d: unexpected error: %v", i, err)
-		}
-		if result != tc.matched {
-			t.Errorf("Test %d: expected match=%t, got %t", i, tc.matched, result)
-		}
+	f, err := os.Create(filepath.Join("testdata", strings.TrimPrefix(tc.expectedPath, "/")))
+	if err != nil {
+		t.Fatalf("could not create test file: %v", err)
+	}
+	defer f.Close()
+	defer os.Remove(f.Name())

-		rel, ok := repl.Get("http.matchers.file.relative")
-		if !ok && result {
-			t.Errorf("Test %d: expected replacer value", i)
-		}
-		if !result {
-			continue
-		}
+	fileMatcherTest(t, 0, tc)
+}

-		if rel != tc.expectedPath {
-			t.Errorf("Test %d: actual path: %v, expected: %v", i, rel, tc.expectedPath)
-		}
+func fileMatcherTest(t *testing.T, i int, tc testCase) {
+	m := &MatchFile{
+		fsmap:    &filesystems.FileSystemMap{},
+		Root:     "./testdata",
+		TryFiles: []string{"{http.request.uri.path}", "{http.request.uri.path}/"},
+	}

-		fileType, _ := repl.Get("http.matchers.file.type")
-		if fileType != tc.expectedType {
-			t.Errorf("Test %d: actual file type: %v, expected: %v", i, fileType, tc.expectedType)
-		}
+	u, err := url.Parse(tc.path)
+	if err != nil {
+		t.Errorf("Test %d: parsing path: %v", i, err)
+	}
+
+	req := &http.Request{URL: u}
+	repl := caddyhttp.NewTestReplacer(req)
+
+	result, err := m.MatchWithError(req)
+	if err != nil {
+		t.Errorf("Test %d: unexpected error: %v", i, err)
+	}
+	if result != tc.matched {
+		t.Errorf("Test %d: expected match=%t, got %t", i, tc.matched, result)
+	}
+
+	rel, ok := repl.Get("http.matchers.file.relative")
+	if !ok && result {
+		t.Errorf("Test %d: expected replacer value", i)
+	}
+	if !result {
+		return
+	}
+
+	if rel != tc.expectedPath {
+		t.Errorf("Test %d: actual path: %v, expected: %v", i, rel, tc.expectedPath)
+	}
+
+	fileType, _ := repl.Get("http.matchers.file.type")
+	if fileType != tc.expectedType {
+		t.Errorf("Test %d: actual file type: %v, expected: %v", i, fileType, tc.expectedType)
 	}
 }

@@ -125,6 +125,11 @@ type FileServer struct {
 	// When possible, all paths are resolved to their absolute form before
 	// comparisons are made. For maximum clarity and explictness, use complete,
 	// absolute paths; or, for greater portability, use relative paths instead.
+	//
+	// Note that hide comparisons are case-sensitive. On case-insensitive
+	// filesystems, requests with different path casing may still resolve to the
+	// same file or directory on disk, so hide should not be treated as a
+	// security boundary for sensitive paths.
 	Hide []string `json:"hide,omitempty"`

 	// The names of files to try as index files if a folder is requested.
@@ -161,11 +161,11 @@ func (ops *HeaderOps) Provision(_ caddy.Context) error {

 // containsPlaceholders checks if the string contains Caddy placeholder syntax {key}
 func containsPlaceholders(s string) bool {
-	openIdx := strings.Index(s, "{")
-	if openIdx == -1 {
+	_, after, ok := strings.Cut(s, "{")
+	if !ok {
 		return false
 	}
-	closeIdx := strings.Index(s[openIdx+1:], "}")
+	closeIdx := strings.Index(after, "}")
 	if closeIdx == -1 {
 		return false
 	}
@@ -262,13 +262,17 @@ func (m MatchHost) Provision(_ caddy.Context) error {
 		if err != nil {
 			return fmt.Errorf("converting hostname '%s' to ASCII: %v", host, err)
 		}
-		if asciiHost != host {
-			m[i] = asciiHost
-		}
 		normalizedHost := strings.ToLower(asciiHost)
 		if firstI, ok := seen[normalizedHost]; ok {
 			return fmt.Errorf("host at index %d is repeated at index %d: %s", firstI, i, host)
 		}
+		// Normalize exact hosts for standardized comparison in large-list fastpath later on.
+		// Keep wildcards/placeholders untouched.
+		if m.fuzzy(asciiHost) {
+			m[i] = asciiHost
+		} else {
+			m[i] = normalizedHost
+		}
 		seen[normalizedHost] = i
 	}

@@ -312,14 +316,15 @@ func (m MatchHost) MatchWithError(r *http.Request) (bool, error) {
 	}

 	if m.large() {
+		reqHostLower := strings.ToLower(reqHost)
 		// fast path: locate exact match using binary search (about 100-1000x faster for large lists)
 		pos := sort.Search(len(m), func(i int) bool {
 			if m.fuzzy(m[i]) {
 				return false
 			}
-			return m[i] >= reqHost
+			return m[i] >= reqHostLower
 		})
-		if pos < len(m) && strings.EqualFold(m[pos], reqHost) {
+		if pos < len(m) && m[pos] == reqHostLower {
 			return true, nil
 		}
 	}
@@ -533,6 +538,7 @@ func (m MatchPath) MatchWithError(r *http.Request) (bool, error) {
 }

 func (MatchPath) matchPatternWithEscapeSequence(escapedPath, matchPath string) bool {
+	escapedPath = strings.ToLower(escapedPath)
 	// We would just compare the pattern against r.URL.Path,
 	// but the pattern contains %, indicating that we should
 	// compare at least some part of the path in raw/escaped
@@ -417,6 +417,11 @@ func TestPathMatcher(t *testing.T) {
 			input:  "/ADMIN%2fpanel",
 			expect: true,
 		},
+		{
+			match:  MatchPath{"/admin%2fpa*el"},
+			input:  "/ADMIN%2fPaAzZLm123NEL",
+			expect: true,
+		},
 	} {
 		err := tc.match.Provision(caddy.Context{})
 		if err == nil && tc.provisionErr {
@@ -962,6 +967,7 @@ func TestVarREMatcher(t *testing.T) {
 		desc       string
 		match      MatchVarsRE
 		input      VarsMiddleware
+		headers    http.Header
 		expect     bool
 		expectRepl map[string]string
 	}{
@@ -996,6 +1002,14 @@ func TestVarREMatcher(t *testing.T) {
 			input:  VarsMiddleware{"Var1": "var1Value"},
 			expect: true,
 		},
+		{
+			desc:       "placeholder key value containing braces is not double-expanded",
+			match:      MatchVarsRE{"{http.request.header.X-Input}": &MatchRegexp{Pattern: ".+", Name: "val"}},
+			input:      VarsMiddleware{},
+			headers:    http.Header{"X-Input": []string{"{env.HOME}"}},
+			expect:     true,
+			expectRepl: map[string]string{"val.0": "{env.HOME}"},
+		},
 	} {
 		t.Run(tc.desc, func(t *testing.T) {
 			t.Parallel()
@@ -1012,7 +1026,7 @@ func TestVarREMatcher(t *testing.T) {
 			}

 			// set up the fake request and its Replacer
-			req := &http.Request{URL: new(url.URL), Method: http.MethodGet}
+			req := &http.Request{URL: new(url.URL), Method: http.MethodGet, Header: tc.headers}
 			repl := caddy.NewReplacer()
 			ctx := context.WithValue(req.Context(), caddy.ReplacerCtxKey, repl)
 			ctx = context.WithValue(ctx, VarsCtxKey, make(map[string]any))
@@ -214,21 +214,24 @@ func serverNameFromContext(ctx context.Context) string {
 	return srv.name
 }

-type metricsInstrumentedHandler struct {
+// metricsInstrumentedRoute wraps a compiled route Handler with metrics
+// instrumentation. It wraps the entire compiled route chain once,
+// collecting metrics only once per route match.
+type metricsInstrumentedRoute struct {
 	handler string
-	mh      MiddlewareHandler
+	next    Handler
 	metrics *Metrics
 }

-func newMetricsInstrumentedHandler(ctx caddy.Context, handler string, mh MiddlewareHandler, metrics *Metrics) *metricsInstrumentedHandler {
-	metrics.init.Do(func() {
-		initHTTPMetrics(ctx, metrics)
+func newMetricsInstrumentedRoute(ctx caddy.Context, handler string, next Handler, m *Metrics) *metricsInstrumentedRoute {
+	m.init.Do(func() {
+		initHTTPMetrics(ctx, m)
 	})

-	return &metricsInstrumentedHandler{handler, mh, metrics}
+	return &metricsInstrumentedRoute{handler: handler, next: next, metrics: m}
 }

-func (h *metricsInstrumentedHandler) ServeHTTP(w http.ResponseWriter, r *http.Request, next Handler) error {
+func (h *metricsInstrumentedRoute) ServeHTTP(w http.ResponseWriter, r *http.Request) error {
 	server := serverNameFromContext(r.Context())
 	labels := prometheus.Labels{"server": server, "handler": h.handler}
 	method := metrics.SanitizeMethod(r.Method)
@@ -267,7 +270,7 @@ func (h *metricsInstrumentedHandler) ServeHTTP(w http.ResponseWriter, r *http.Re
 		return false
 	})
 	wrec := NewResponseRecorder(w, nil, writeHeaderRecorder)
-	err := h.mh.ServeHTTP(wrec, r, next)
+	err := h.next.ServeHTTP(wrec, r)
 	dur := time.Since(start).Seconds()
 	h.metrics.httpMetrics.requestCount.With(labels).Inc()

@@ -47,16 +47,12 @@ func TestMetricsInstrumentedHandler(t *testing.T) {
 		return handlerErr
 	})

-	mh := middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
-		return h.ServeHTTP(w, r)
-	})
-
-	ih := newMetricsInstrumentedHandler(ctx, "bar", mh, metrics)
+	ih := newMetricsInstrumentedRoute(ctx, "bar", h, metrics)

 	r := httptest.NewRequest("GET", "/", nil)
 	w := httptest.NewRecorder()

-	if actual := ih.ServeHTTP(w, r, h); actual != handlerErr {
+	if actual := ih.ServeHTTP(w, r); actual != handlerErr {
 		t.Errorf("Not same: expected %#v, but got %#v", handlerErr, actual)
 	}
 	if actual := testutil.ToFloat64(metrics.httpMetrics.requestInFlight); actual != 0.0 {
@@ -64,19 +60,19 @@ func TestMetricsInstrumentedHandler(t *testing.T) {
 	}

 	handlerErr = nil
-	if err := ih.ServeHTTP(w, r, h); err != nil {
+	if err := ih.ServeHTTP(w, r); err != nil {
 		t.Errorf("Received unexpected error: %v", err)
 	}

 	// an empty handler - no errors, no header written
-	mh = middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
+	emptyHandler := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
 		return nil
 	})
-	ih = newMetricsInstrumentedHandler(ctx, "empty", mh, metrics)
+	ih = newMetricsInstrumentedRoute(ctx, "empty", emptyHandler, metrics)
 	r = httptest.NewRequest("GET", "/", nil)
 	w = httptest.NewRecorder()

-	if err := ih.ServeHTTP(w, r, h); err != nil {
+	if err := ih.ServeHTTP(w, r); err != nil {
 		t.Errorf("Received unexpected error: %v", err)
 	}
 	if actual := w.Result().StatusCode; actual != 200 {
@@ -87,16 +83,16 @@ func TestMetricsInstrumentedHandler(t *testing.T) {
 	}

 	// handler returning an error with an HTTP status
-	mh = middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
+	errHandler := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
 		return Error(http.StatusTooManyRequests, nil)
 	})

-	ih = newMetricsInstrumentedHandler(ctx, "foo", mh, metrics)
+	ih = newMetricsInstrumentedRoute(ctx, "foo", errHandler, metrics)

 	r = httptest.NewRequest("GET", "/", nil)
 	w = httptest.NewRecorder()

-	if err := ih.ServeHTTP(w, r, nil); err == nil {
+	if err := ih.ServeHTTP(w, r); err == nil {
 		t.Errorf("expected error to be propagated")
 	}

@@ -225,16 +221,12 @@ func TestMetricsInstrumentedHandlerPerHost(t *testing.T) {
 		return handlerErr
 	})

-	mh := middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
-		return h.ServeHTTP(w, r)
-	})
-
-	ih := newMetricsInstrumentedHandler(ctx, "bar", mh, metrics)
+	ih := newMetricsInstrumentedRoute(ctx, "bar", h, metrics)

 	r := httptest.NewRequest("GET", "/", nil)
 	w := httptest.NewRecorder()

-	if actual := ih.ServeHTTP(w, r, h); actual != handlerErr {
+	if actual := ih.ServeHTTP(w, r); actual != handlerErr {
 		t.Errorf("Not same: expected %#v, but got %#v", handlerErr, actual)
 	}
 	if actual := testutil.ToFloat64(metrics.httpMetrics.requestInFlight); actual != 0.0 {
@@ -242,19 +234,19 @@ func TestMetricsInstrumentedHandlerPerHost(t *testing.T) {
 	}

 	handlerErr = nil
-	if err := ih.ServeHTTP(w, r, h); err != nil {
+	if err := ih.ServeHTTP(w, r); err != nil {
 		t.Errorf("Received unexpected error: %v", err)
 	}

 	// an empty handler - no errors, no header written
-	mh = middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
+	emptyHandler := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
 		return nil
 	})
-	ih = newMetricsInstrumentedHandler(ctx, "empty", mh, metrics)
+	ih = newMetricsInstrumentedRoute(ctx, "empty", emptyHandler, metrics)
 	r = httptest.NewRequest("GET", "/", nil)
 	w = httptest.NewRecorder()

-	if err := ih.ServeHTTP(w, r, h); err != nil {
+	if err := ih.ServeHTTP(w, r); err != nil {
 		t.Errorf("Received unexpected error: %v", err)
 	}
 	if actual := w.Result().StatusCode; actual != 200 {
@@ -265,16 +257,16 @@ func TestMetricsInstrumentedHandlerPerHost(t *testing.T) {
 	}

 	// handler returning an error with an HTTP status
-	mh = middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
+	errHandler := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
 		return Error(http.StatusTooManyRequests, nil)
 	})

-	ih = newMetricsInstrumentedHandler(ctx, "foo", mh, metrics)
+	ih = newMetricsInstrumentedRoute(ctx, "foo", errHandler, metrics)

 	r = httptest.NewRequest("GET", "/", nil)
 	w = httptest.NewRecorder()

-	if err := ih.ServeHTTP(w, r, nil); err == nil {
+	if err := ih.ServeHTTP(w, r); err == nil {
 		t.Errorf("expected error to be propagated")
 	}

@@ -397,30 +389,30 @@ func TestMetricsCardinalityProtection(t *testing.T) {
 	// Add one allowed host
 	metrics.allowedHosts["allowed.com"] = struct{}{}

-	mh := middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
+	h := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
 		w.Write([]byte("hello"))
 		return nil
 	})

-	ih := newMetricsInstrumentedHandler(ctx, "test", mh, metrics)
+	ih := newMetricsInstrumentedRoute(ctx, "test", h, metrics)

 	// Test request to allowed host
 	r1 := httptest.NewRequest("GET", "http://allowed.com/", nil)
 	r1.Host = "allowed.com"
 	w1 := httptest.NewRecorder()
-	ih.ServeHTTP(w1, r1, HandlerFunc(func(w http.ResponseWriter, r *http.Request) error { return nil }))
+	ih.ServeHTTP(w1, r1)

 	// Test request to unknown host (should be mapped to "_other")
 	r2 := httptest.NewRequest("GET", "http://attacker.com/", nil)
 	r2.Host = "attacker.com"
 	w2 := httptest.NewRecorder()
-	ih.ServeHTTP(w2, r2, HandlerFunc(func(w http.ResponseWriter, r *http.Request) error { return nil }))
+	ih.ServeHTTP(w2, r2)

 	// Test request to another unknown host (should also be mapped to "_other")
 	r3 := httptest.NewRequest("GET", "http://evil.com/", nil)
 	r3.Host = "evil.com"
 	w3 := httptest.NewRecorder()
-	ih.ServeHTTP(w3, r3, HandlerFunc(func(w http.ResponseWriter, r *http.Request) error { return nil }))
+	ih.ServeHTTP(w3, r3)

 	// Check that metrics contain:
 	// - One entry for "allowed.com"
@@ -452,26 +444,26 @@ func TestMetricsHTTPSCatchAll(t *testing.T) {
 		allowedHosts:         make(map[string]struct{}), // Empty - no explicitly allowed hosts
 	}

-	mh := middlewareHandlerFunc(func(w http.ResponseWriter, r *http.Request, h Handler) error {
+	h := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
 		w.Write([]byte("hello"))
 		return nil
 	})

-	ih := newMetricsInstrumentedHandler(ctx, "test", mh, metrics)
+	ih := newMetricsInstrumentedRoute(ctx, "test", h, metrics)

 	// Test HTTPS request (should be allowed even though not in allowedHosts)
 	r1 := httptest.NewRequest("GET", "https://unknown.com/", nil)
 	r1.Host = "unknown.com"
 	r1.TLS = &tls.ConnectionState{} // Mark as TLS/HTTPS
 	w1 := httptest.NewRecorder()
-	ih.ServeHTTP(w1, r1, HandlerFunc(func(w http.ResponseWriter, r *http.Request) error { return nil }))
+	ih.ServeHTTP(w1, r1)

 	// Test HTTP request (should be mapped to "_other")
 	r2 := httptest.NewRequest("GET", "http://unknown.com/", nil)
 	r2.Host = "unknown.com"
 	// No TLS field = HTTP request
 	w2 := httptest.NewRecorder()
-	ih.ServeHTTP(w2, r2, HandlerFunc(func(w http.ResponseWriter, r *http.Request) error { return nil }))
+	ih.ServeHTTP(w2, r2)

 	// Check that HTTPS request gets real host, HTTP gets "_other"
 	expected := `
@@ -488,8 +480,102 @@ func TestMetricsHTTPSCatchAll(t *testing.T) {
 	}
 }

-type middlewareHandlerFunc func(http.ResponseWriter, *http.Request, Handler) error
+func TestMetricsInstrumentedRoute(t *testing.T) {
+	ctx, _ := caddy.NewContext(caddy.Context{Context: context.Background()})
+	m := &Metrics{
+		init:        sync.Once{},
+		httpMetrics: &httpMetrics{},
+	}

-func (f middlewareHandlerFunc) ServeHTTP(w http.ResponseWriter, r *http.Request, h Handler) error {
-	return f(w, r, h)
+	handlerErr := errors.New("oh noes")
+	response := []byte("hello world!")
+	innerHandler := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
+		if actual := testutil.ToFloat64(m.httpMetrics.requestInFlight); actual != 1.0 {
+			t.Errorf("Expected requestInFlight to be 1.0, got %v", actual)
+		}
+		if handlerErr == nil {
+			w.Write(response)
+		}
+		return handlerErr
+	})
+
+	ih := newMetricsInstrumentedRoute(ctx, "test_handler", innerHandler, m)
+
+	r := httptest.NewRequest("GET", "/", nil)
+	w := httptest.NewRecorder()
+
+	// Test with error
+	if actual := ih.ServeHTTP(w, r); actual != handlerErr {
+		t.Errorf("Expected error %v, got %v", handlerErr, actual)
+	}
+	if actual := testutil.ToFloat64(m.httpMetrics.requestInFlight); actual != 0.0 {
+		t.Errorf("Expected requestInFlight to be 0.0 after request, got %v", actual)
+	}
+	if actual := testutil.ToFloat64(m.httpMetrics.requestErrors); actual != 1.0 {
+		t.Errorf("Expected requestErrors to be 1.0, got %v", actual)
+	}
+
+	// Test without error
+	handlerErr = nil
+	w = httptest.NewRecorder()
+	if err := ih.ServeHTTP(w, r); err != nil {
+		t.Errorf("Unexpected error: %v", err)
+	}
+}
+
+func BenchmarkMetricsInstrumentedRoute(b *testing.B) {
+	ctx, _ := caddy.NewContext(caddy.Context{Context: context.Background()})
+	m := &Metrics{
+		init:        sync.Once{},
+		httpMetrics: &httpMetrics{},
+	}
+
+	noopHandler := HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
+		w.Write([]byte("ok"))
+		return nil
+	})
+
+	ih := newMetricsInstrumentedRoute(ctx, "bench_handler", noopHandler, m)
+
+	r := httptest.NewRequest("GET", "/", nil)
+	w := httptest.NewRecorder()
+
+	b.ResetTimer()
+	b.ReportAllocs()
+	for i := 0; i < b.N; i++ {
+		ih.ServeHTTP(w, r)
+	}
+}
+
+// BenchmarkSingleRouteMetrics simulates the new behavior where metrics
+// are collected once for the entire route.
+func BenchmarkSingleRouteMetrics(b *testing.B) {
+	ctx, _ := caddy.NewContext(caddy.Context{Context: context.Background()})
+	m := &Metrics{
+		init:        sync.Once{},
+		httpMetrics: &httpMetrics{},
+	}
+
+	// Build a chain of 5 plain middleware handlers (no per-handler metrics)
+	var next Handler = HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
+		return nil
+	})
+	for i := 0; i < 5; i++ {
+		capturedNext := next
+		next = HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
+			return capturedNext.ServeHTTP(w, r)
+		})
+	}
+
+	// Wrap the entire chain with a single route-level metrics handler
+	ih := newMetricsInstrumentedRoute(ctx, "handler", next, m)
+
+	r := httptest.NewRequest("GET", "/", nil)
+	w := httptest.NewRecorder()
+
+	b.ResetTimer()
+	b.ReportAllocs()
+	for i := 0; i < b.N; i++ {
+		ih.ServeHTTP(w, r)
+	}
 }
@@ -420,7 +420,16 @@ func getReqTLSReplacement(req *http.Request, key string) (any, bool) {
 	if strings.HasPrefix(field, "client.") {
 		cert := getTLSPeerCert(req.TLS)
 		if cert == nil {
-			return nil, false
+			// Instead of returning (nil, false) here, we set it to a dummy
+			// value to fix #7530. This way, even if there is no client cert,
+			// evaluating placeholders with ReplaceKnown() will still remove
+			// the placeholder, which would be expected. It is not expected
+			// for the placeholder to sometimes get removed based on whether
+			// the client presented a cert. We also do not return true here
+			// because we probably should remain accurate about whether a
+			// placeholder is, in fact, known or not.
+			// (This allocation may be slightly inefficient.)
+			cert = new(x509.Certificate)
 		}

 		// subject alternate names (SANs)
@@ -73,8 +73,9 @@ func (adminUpstreams) handleUpstreams(w http.ResponseWriter, r *http.Request) er

 	// Collect the results to respond with
 	results := []upstreamStatus{}
+	knownHosts := make(map[string]struct{})

-	// Iterate over the upstream pool (needs to be fast)
+	// Iterate over the static upstream pool (needs to be fast)
 	var rangeErr error
 	hosts.Range(func(key, val any) bool {
 		address, ok := key.(string)
@@ -95,6 +96,8 @@ func (adminUpstreams) handleUpstreams(w http.ResponseWriter, r *http.Request) er
 			return false
 		}

+		knownHosts[address] = struct{}{}
+
 		results = append(results, upstreamStatus{
 			Address:     address,
 			NumRequests: upstream.NumRequests(),
@@ -103,11 +106,32 @@ func (adminUpstreams) handleUpstreams(w http.ResponseWriter, r *http.Request) er
 		return true
 	})

-	// If an error happened during the range, return it
+	currentInFlight := getInFlightRequests()
+	for address, count := range currentInFlight {
+		if _, exists := knownHosts[address]; !exists && count > 0 {
+			results = append(results, upstreamStatus{
+				Address:     address,
+				NumRequests: int(count),
+				Fails:       0,
+			})
+		}
+	}
+
 	if rangeErr != nil {
 		return rangeErr
 	}

+	// Also include dynamic upstreams
+	dynamicHostsMu.RLock()
+	for address, entry := range dynamicHosts {
+		results = append(results, upstreamStatus{
+			Address:     address,
+			NumRequests: entry.host.NumRequests(),
+			Fails:       entry.host.Fails(),
+		})
+	}
+	dynamicHostsMu.RUnlock()
+
 	err := enc.Encode(results)
 	if err != nil {
 		return caddy.APIError{
@@ -0,0 +1,275 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package reverseproxy
+
+import (
+	"encoding/json"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+	"time"
+)
+
+// adminHandlerFixture sets up the global host state for an admin endpoint test
+// and returns a cleanup function that must be deferred by the caller.
+//
+// staticAddrs are inserted into the UsagePool (as a static upstream would be).
+// dynamicAddrs are inserted into the dynamicHosts map (as a dynamic upstream would be).
+func adminHandlerFixture(t *testing.T, staticAddrs, dynamicAddrs []string) func() {
+	t.Helper()
+
+	for _, addr := range staticAddrs {
+		u := &Upstream{Dial: addr}
+		u.fillHost()
+	}
+
+	dynamicHostsMu.Lock()
+	for _, addr := range dynamicAddrs {
+		dynamicHosts[addr] = dynamicHostEntry{host: new(Host), lastSeen: time.Now()}
+	}
+	dynamicHostsMu.Unlock()
+
+	return func() {
+		// Remove static entries from the UsagePool.
+		for _, addr := range staticAddrs {
+			_, _ = hosts.Delete(addr)
+		}
+		// Remove dynamic entries.
+		dynamicHostsMu.Lock()
+		for _, addr := range dynamicAddrs {
+			delete(dynamicHosts, addr)
+		}
+		dynamicHostsMu.Unlock()
+	}
+}
+
+// callAdminUpstreams fires a GET against handleUpstreams and returns the
+// decoded response body.
+func callAdminUpstreams(t *testing.T) []upstreamStatus {
+	t.Helper()
+	req := httptest.NewRequest(http.MethodGet, "/reverse_proxy/upstreams", nil)
+	w := httptest.NewRecorder()
+
+	handler := adminUpstreams{}
+	if err := handler.handleUpstreams(w, req); err != nil {
+		t.Fatalf("handleUpstreams returned unexpected error: %v", err)
+	}
+	if w.Code != http.StatusOK {
+		t.Fatalf("expected 200, got %d", w.Code)
+	}
+	if ct := w.Header().Get("Content-Type"); ct != "application/json" {
+		t.Fatalf("expected Content-Type application/json, got %q", ct)
+	}
+
+	var results []upstreamStatus
+	if err := json.NewDecoder(w.Body).Decode(&results); err != nil {
+		t.Fatalf("failed to decode response: %v", err)
+	}
+	return results
+}
+
+// resultsByAddress indexes a slice of upstreamStatus by address for easier
+// lookup in assertions.
+func resultsByAddress(statuses []upstreamStatus) map[string]upstreamStatus {
+	m := make(map[string]upstreamStatus, len(statuses))
+	for _, s := range statuses {
+		m[s.Address] = s
+	}
+	return m
+}
+
+// TestAdminUpstreamsMethodNotAllowed verifies that non-GET methods are rejected.
+func TestAdminUpstreamsMethodNotAllowed(t *testing.T) {
+	for _, method := range []string{http.MethodPost, http.MethodPut, http.MethodDelete} {
+		req := httptest.NewRequest(method, "/reverse_proxy/upstreams", nil)
+		w := httptest.NewRecorder()
+		err := (adminUpstreams{}).handleUpstreams(w, req)
+		if err == nil {
+			t.Errorf("method %s: expected an error, got nil", method)
+			continue
+		}
+		apiErr, ok := err.(interface{ HTTPStatus() int })
+		if !ok {
+			// caddy.APIError stores the code in HTTPStatus field, access via the
+			// exported interface it satisfies indirectly; just check non-nil.
+			continue
+		}
+		if code := apiErr.HTTPStatus(); code != http.StatusMethodNotAllowed {
+			t.Errorf("method %s: expected 405, got %d", method, code)
+		}
+	}
+}
+
+// TestAdminUpstreamsEmpty verifies that an empty response is valid JSON when
+// no upstreams are registered.
+func TestAdminUpstreamsEmpty(t *testing.T) {
+	resetDynamicHosts()
+
+	results := callAdminUpstreams(t)
+	if results == nil {
+		t.Error("expected non-nil (empty) slice, got nil")
+	}
+	if len(results) != 0 {
+		t.Errorf("expected 0 results with empty pools, got %d", len(results))
+	}
+}
+
+// TestAdminUpstreamsStaticOnly verifies that static upstreams (from the
+// UsagePool) appear in the response with correct addresses.
+func TestAdminUpstreamsStaticOnly(t *testing.T) {
+	resetDynamicHosts()
+	cleanup := adminHandlerFixture(t,
+		[]string{"10.0.0.1:80", "10.0.0.2:80"},
+		nil,
+	)
+	defer cleanup()
+
+	results := callAdminUpstreams(t)
+	byAddr := resultsByAddress(results)
+
+	for _, addr := range []string{"10.0.0.1:80", "10.0.0.2:80"} {
+		if _, ok := byAddr[addr]; !ok {
+			t.Errorf("expected static upstream %q in response", addr)
+		}
+	}
+	if len(results) != 2 {
+		t.Errorf("expected exactly 2 results, got %d", len(results))
+	}
+}
+
+// TestAdminUpstreamsDynamicOnly verifies that dynamic upstreams (from
+// dynamicHosts) appear in the response with correct addresses.
+func TestAdminUpstreamsDynamicOnly(t *testing.T) {
+	resetDynamicHosts()
+	cleanup := adminHandlerFixture(t,
+		nil,
+		[]string{"10.0.1.1:80", "10.0.1.2:80"},
+	)
+	defer cleanup()
+
+	results := callAdminUpstreams(t)
+	byAddr := resultsByAddress(results)
+
+	for _, addr := range []string{"10.0.1.1:80", "10.0.1.2:80"} {
+		if _, ok := byAddr[addr]; !ok {
+			t.Errorf("expected dynamic upstream %q in response", addr)
+		}
+	}
+	if len(results) != 2 {
+		t.Errorf("expected exactly 2 results, got %d", len(results))
+	}
+}
+
+// TestAdminUpstreamsBothPools verifies that static and dynamic upstreams are
+// both present in the same response and that there is no overlap or omission.
+func TestAdminUpstreamsBothPools(t *testing.T) {
+	resetDynamicHosts()
+	cleanup := adminHandlerFixture(t,
+		[]string{"10.0.2.1:80"},
+		[]string{"10.0.2.2:80"},
+	)
+	defer cleanup()
+
+	results := callAdminUpstreams(t)
+	if len(results) != 2 {
+		t.Fatalf("expected 2 results (1 static + 1 dynamic), got %d", len(results))
+	}
+
+	byAddr := resultsByAddress(results)
+	if _, ok := byAddr["10.0.2.1:80"]; !ok {
+		t.Error("static upstream missing from response")
+	}
+	if _, ok := byAddr["10.0.2.2:80"]; !ok {
+		t.Error("dynamic upstream missing from response")
+	}
+}
+
+// TestAdminUpstreamsNoOverlapBetweenPools verifies that an address registered
+// only as a static upstream does not also appear as a dynamic entry, and
+// vice-versa.
+func TestAdminUpstreamsNoOverlapBetweenPools(t *testing.T) {
+	resetDynamicHosts()
+	cleanup := adminHandlerFixture(t,
+		[]string{"10.0.3.1:80"},
+		[]string{"10.0.3.2:80"},
+	)
+	defer cleanup()
+
+	results := callAdminUpstreams(t)
+	seen := make(map[string]int)
+	for _, r := range results {
+		seen[r.Address]++
+	}
+	for addr, count := range seen {
+		if count > 1 {
+			t.Errorf("address %q appeared %d times; expected exactly once", addr, count)
+		}
+	}
+}
+
+// TestAdminUpstreamsReportsFailCounts verifies that fail counts accumulated on
+// a dynamic upstream's Host are reflected in the response.
+func TestAdminUpstreamsReportsFailCounts(t *testing.T) {
+	resetDynamicHosts()
+
+	const addr = "10.0.4.1:80"
+	h := new(Host)
+	_ = h.countFail(3)
+
+	dynamicHostsMu.Lock()
+	dynamicHosts[addr] = dynamicHostEntry{host: h, lastSeen: time.Now()}
+	dynamicHostsMu.Unlock()
+	defer func() {
+		dynamicHostsMu.Lock()
+		delete(dynamicHosts, addr)
+		dynamicHostsMu.Unlock()
+	}()
+
+	results := callAdminUpstreams(t)
+	byAddr := resultsByAddress(results)
+
+	status, ok := byAddr[addr]
+	if !ok {
+		t.Fatalf("expected %q in response", addr)
+	}
+	if status.Fails != 3 {
+		t.Errorf("expected Fails=3, got %d", status.Fails)
+	}
+}
+
+// TestAdminUpstreamsReportsNumRequests verifies that the active request count
+// for a static upstream is reflected in the response.
+func TestAdminUpstreamsReportsNumRequests(t *testing.T) {
+	resetDynamicHosts()
+
+	const addr = "10.0.4.2:80"
+	u := &Upstream{Dial: addr}
+	u.fillHost()
+	defer func() { _, _ = hosts.Delete(addr) }()
+
+	_ = u.Host.countRequest(2)
+	defer func() { _ = u.Host.countRequest(-2) }()
+
+	results := callAdminUpstreams(t)
+	byAddr := resultsByAddress(results)
+
+	status, ok := byAddr[addr]
+	if !ok {
+		t.Fatalf("expected %q in response", addr)
+	}
+	if status.NumRequests != 2 {
+		t.Errorf("expected NumRequests=2, got %d", status.NumRequests)
+	}
+}
@@ -0,0 +1,345 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package reverseproxy
+
+import (
+	"sync"
+	"testing"
+	"time"
+
+	"github.com/caddyserver/caddy/v2"
+)
+
+// resetDynamicHosts clears global dynamic host state between tests.
+func resetDynamicHosts() {
+	dynamicHostsMu.Lock()
+	dynamicHosts = make(map[string]dynamicHostEntry)
+	dynamicHostsMu.Unlock()
+	// Reset the Once so cleanup goroutine tests can re-trigger if needed.
+	dynamicHostsCleanerOnce = sync.Once{}
+}
+
+// TestFillDynamicHostCreatesEntry verifies that calling fillDynamicHost on a
+// new address inserts an entry into dynamicHosts and assigns a non-nil Host.
+func TestFillDynamicHostCreatesEntry(t *testing.T) {
+	resetDynamicHosts()
+
+	u := &Upstream{Dial: "192.0.2.1:80"}
+	u.fillDynamicHost()
+
+	if u.Host == nil {
+		t.Fatal("expected Host to be set after fillDynamicHost")
+	}
+
+	dynamicHostsMu.RLock()
+	entry, ok := dynamicHosts["192.0.2.1:80"]
+	dynamicHostsMu.RUnlock()
+
+	if !ok {
+		t.Fatal("expected entry in dynamicHosts map")
+	}
+	if entry.host != u.Host {
+		t.Error("dynamicHosts entry host should be the same pointer assigned to Upstream.Host")
+	}
+	if entry.lastSeen.IsZero() {
+		t.Error("expected lastSeen to be set")
+	}
+}
+
+// TestFillDynamicHostReusesSameHost verifies that two calls for the same address
+// return the exact same *Host pointer so that state (e.g. fail counts) is shared.
+func TestFillDynamicHostReusesSameHost(t *testing.T) {
+	resetDynamicHosts()
+
+	u1 := &Upstream{Dial: "192.0.2.2:80"}
+	u1.fillDynamicHost()
+
+	u2 := &Upstream{Dial: "192.0.2.2:80"}
+	u2.fillDynamicHost()
+
+	if u1.Host != u2.Host {
+		t.Error("expected both upstreams to share the same *Host pointer")
+	}
+}
+
+// TestFillDynamicHostUpdatesLastSeen verifies that a second call for the same
+// address advances the lastSeen timestamp.
+func TestFillDynamicHostUpdatesLastSeen(t *testing.T) {
+	resetDynamicHosts()
+
+	u := &Upstream{Dial: "192.0.2.3:80"}
+	u.fillDynamicHost()
+
+	dynamicHostsMu.RLock()
+	first := dynamicHosts["192.0.2.3:80"].lastSeen
+	dynamicHostsMu.RUnlock()
+
+	// Ensure measurable time passes.
+	time.Sleep(2 * time.Millisecond)
+
+	u2 := &Upstream{Dial: "192.0.2.3:80"}
+	u2.fillDynamicHost()
+
+	dynamicHostsMu.RLock()
+	second := dynamicHosts["192.0.2.3:80"].lastSeen
+	dynamicHostsMu.RUnlock()
+
+	if !second.After(first) {
+		t.Error("expected lastSeen to be updated on second fillDynamicHost call")
+	}
+}
+
+// TestFillDynamicHostIndependentAddresses verifies that different addresses get
+// independent Host entries.
+func TestFillDynamicHostIndependentAddresses(t *testing.T) {
+	resetDynamicHosts()
+
+	u1 := &Upstream{Dial: "192.0.2.4:80"}
+	u1.fillDynamicHost()
+
+	u2 := &Upstream{Dial: "192.0.2.5:80"}
+	u2.fillDynamicHost()
+
+	if u1.Host == u2.Host {
+		t.Error("different addresses should have different *Host entries")
+	}
+}
+
+// TestFillDynamicHostPreservesFailCount verifies that fail counts on a dynamic
+// host survive across multiple fillDynamicHost calls (simulating sequential
+// requests), which is the core behaviour fixed by this change.
+func TestFillDynamicHostPreservesFailCount(t *testing.T) {
+	resetDynamicHosts()
+
+	// First "request": provision and record a failure.
+	u1 := &Upstream{Dial: "192.0.2.6:80"}
+	u1.fillDynamicHost()
+	_ = u1.Host.countFail(1)
+
+	if u1.Host.Fails() != 1 {
+		t.Fatalf("expected 1 fail, got %d", u1.Host.Fails())
+	}
+
+	// Second "request": provision the same address again (new *Upstream, same address).
+	u2 := &Upstream{Dial: "192.0.2.6:80"}
+	u2.fillDynamicHost()
+
+	if u2.Host.Fails() != 1 {
+		t.Errorf("expected fail count to persist across fillDynamicHost calls, got %d", u2.Host.Fails())
+	}
+}
+
+// TestProvisionUpstreamDynamic verifies that provisionUpstream with dynamic=true
+// uses fillDynamicHost (not the UsagePool) and sets healthCheckPolicy /
+// MaxRequests correctly from handler config.
+func TestProvisionUpstreamDynamic(t *testing.T) {
+	resetDynamicHosts()
+
+	passive := &PassiveHealthChecks{
+		FailDuration:          caddy.Duration(10 * time.Second),
+		MaxFails:              3,
+		UnhealthyRequestCount: 5,
+	}
+	h := Handler{
+		HealthChecks: &HealthChecks{
+			Passive: passive,
+		},
+	}
+
+	u := &Upstream{Dial: "192.0.2.7:80"}
+	h.provisionUpstream(u, true)
+
+	if u.Host == nil {
+		t.Fatal("Host should be set after provisionUpstream")
+	}
+	if u.healthCheckPolicy != passive {
+		t.Error("healthCheckPolicy should point to the handler's PassiveHealthChecks")
+	}
+	if u.MaxRequests != 5 {
+		t.Errorf("expected MaxRequests=5 from UnhealthyRequestCount, got %d", u.MaxRequests)
+	}
+
+	// Must be in dynamicHosts, not in the static UsagePool.
+	dynamicHostsMu.RLock()
+	_, inDynamic := dynamicHosts["192.0.2.7:80"]
+	dynamicHostsMu.RUnlock()
+	if !inDynamic {
+		t.Error("dynamic upstream should be stored in dynamicHosts")
+	}
+	_, inPool := hosts.References("192.0.2.7:80")
+	if inPool {
+		t.Error("dynamic upstream should NOT be stored in the static UsagePool")
+	}
+}
+
+// TestProvisionUpstreamStatic verifies that provisionUpstream with dynamic=false
+// uses the UsagePool and does NOT insert into dynamicHosts.
+func TestProvisionUpstreamStatic(t *testing.T) {
+	resetDynamicHosts()
+
+	h := Handler{}
+
+	u := &Upstream{Dial: "192.0.2.8:80"}
+	h.provisionUpstream(u, false)
+
+	if u.Host == nil {
+		t.Fatal("Host should be set after provisionUpstream")
+	}
+
+	refs, inPool := hosts.References("192.0.2.8:80")
+	if !inPool {
+		t.Error("static upstream should be in the UsagePool")
+	}
+	if refs != 1 {
+		t.Errorf("expected ref count 1, got %d", refs)
+	}
+
+	dynamicHostsMu.RLock()
+	_, inDynamic := dynamicHosts["192.0.2.8:80"]
+	dynamicHostsMu.RUnlock()
+	if inDynamic {
+		t.Error("static upstream should NOT be in dynamicHosts")
+	}
+
+	// Clean up the pool entry we just added.
+	_, _ = hosts.Delete("192.0.2.8:80")
+}
+
+// TestDynamicHostHealthyConsultsFails verifies the end-to-end passive health
+// check path: after enough failures are recorded against a dynamic upstream's
+// shared *Host, Healthy() returns false for a newly provisioned *Upstream with
+// the same address.
+func TestDynamicHostHealthyConsultsFails(t *testing.T) {
+	resetDynamicHosts()
+
+	passive := &PassiveHealthChecks{
+		FailDuration: caddy.Duration(time.Minute),
+		MaxFails:     2,
+	}
+	h := Handler{
+		HealthChecks: &HealthChecks{Passive: passive},
+	}
+
+	// First request: provision and record two failures.
+	u1 := &Upstream{Dial: "192.0.2.9:80"}
+	h.provisionUpstream(u1, true)
+
+	_ = u1.Host.countFail(1)
+	_ = u1.Host.countFail(1)
+
+	// Second request: fresh *Upstream, same address.
+	u2 := &Upstream{Dial: "192.0.2.9:80"}
+	h.provisionUpstream(u2, true)
+
+	if u2.Healthy() {
+		t.Error("upstream should be unhealthy after MaxFails failures have been recorded against its shared Host")
+	}
+}
+
+// TestDynamicHostCleanupEvictsStaleEntries verifies that the cleanup sweep
+// removes entries whose lastSeen is older than dynamicHostIdleExpiry.
+func TestDynamicHostCleanupEvictsStaleEntries(t *testing.T) {
+	resetDynamicHosts()
+
+	const addr = "192.0.2.10:80"
+
+	// Insert an entry directly with a lastSeen far in the past.
+	dynamicHostsMu.Lock()
+	dynamicHosts[addr] = dynamicHostEntry{
+		host:     new(Host),
+		lastSeen: time.Now().Add(-2 * dynamicHostIdleExpiry),
+	}
+	dynamicHostsMu.Unlock()
+
+	// Run the cleanup logic inline (same logic as the goroutine).
+	dynamicHostsMu.Lock()
+	for a, entry := range dynamicHosts {
+		if time.Since(entry.lastSeen) > dynamicHostIdleExpiry {
+			delete(dynamicHosts, a)
+		}
+	}
+	dynamicHostsMu.Unlock()
+
+	dynamicHostsMu.RLock()
+	_, stillPresent := dynamicHosts[addr]
+	dynamicHostsMu.RUnlock()
+
+	if stillPresent {
+		t.Error("stale dynamic host entry should have been evicted by cleanup sweep")
+	}
+}
+
+// TestDynamicHostCleanupRetainsFreshEntries verifies that the cleanup sweep
+// keeps entries whose lastSeen is within dynamicHostIdleExpiry.
+func TestDynamicHostCleanupRetainsFreshEntries(t *testing.T) {
+	resetDynamicHosts()
+
+	const addr = "192.0.2.11:80"
+
+	dynamicHostsMu.Lock()
+	dynamicHosts[addr] = dynamicHostEntry{
+		host:     new(Host),
+		lastSeen: time.Now(),
+	}
+	dynamicHostsMu.Unlock()
+
+	// Run the cleanup logic inline.
+	dynamicHostsMu.Lock()
+	for a, entry := range dynamicHosts {
+		if time.Since(entry.lastSeen) > dynamicHostIdleExpiry {
+			delete(dynamicHosts, a)
+		}
+	}
+	dynamicHostsMu.Unlock()
+
+	dynamicHostsMu.RLock()
+	_, stillPresent := dynamicHosts[addr]
+	dynamicHostsMu.RUnlock()
+
+	if !stillPresent {
+		t.Error("fresh dynamic host entry should be retained by cleanup sweep")
+	}
+}
+
+// TestDynamicHostConcurrentFillHost verifies that concurrent calls to
+// fillDynamicHost for the same address all get the same *Host pointer and
+// don't race (run with -race).
+func TestDynamicHostConcurrentFillHost(t *testing.T) {
+	resetDynamicHosts()
+
+	const addr = "192.0.2.12:80"
+	const goroutines = 50
+
+	var wg sync.WaitGroup
+	hosts := make([]*Host, goroutines)
+
+	for i := range goroutines {
+		wg.Add(1)
+		go func(idx int) {
+			defer wg.Done()
+			u := &Upstream{Dial: addr}
+			u.fillDynamicHost()
+			hosts[idx] = u.Host
+		}(i)
+	}
+	wg.Wait()
+
+	first := hosts[0]
+	for i, h := range hosts {
+		if h != first {
+			t.Errorf("goroutine %d got a different *Host pointer; expected all to share the same entry", i)
+		}
+	}
+}
@@ -442,7 +442,7 @@ func (t Transport) splitPos(path string) int {
 	for _, split := range t.SplitPath {
 		splitLen := len(split)

-		for i := 0; i < pathLen; i++ {
+		for i := range pathLen {
 			if path[i] >= utf8.RuneSelf {
 				if _, end := splitSearchNonASCII.IndexString(path, split); end > -1 {
 					return end
@@ -456,7 +456,7 @@ func (t Transport) splitPos(path string) int {
 			}

 			match := true
-			for j := 0; j < splitLen; j++ {
+			for j := range splitLen {
 				c := path[i+j]

 				if c >= utf8.RuneSelf {
@@ -208,6 +208,24 @@ func parseCaddyfile(h httpcaddyfile.Helper) ([]httpcaddyfile.ConfigValue, error)
 	for _, from := range sortedHeadersToCopy {
 		to := http.CanonicalHeaderKey(headersToCopy[from])
 		placeholderName := "http.reverse_proxy.header." + http.CanonicalHeaderKey(from)
+
+		// Always delete the client-supplied header before conditionally setting
+		// it from the auth response. Without this, a client that pre-supplies a
+		// header listed in copy_headers can inject arbitrary values when the auth
+		// service does not return that header: the MatchNot guard below would
+		// skip the Set entirely, leaving the original client-controlled value
+		// intact and forwarding it to the backend.
+		copyHeaderRoutes = append(copyHeaderRoutes, caddyhttp.Route{
+			HandlersRaw: []json.RawMessage{caddyconfig.JSONModuleObject(
+				&headers.Handler{
+					Request: &headers.HeaderOps{
+						Delete: []string{to},
+					},
+				},
+				"handler", "headers", nil,
+			)},
+		})
+
 		handler := &headers.Handler{
 			Request: &headers.HeaderOps{
 				Set: http.Header{
@@ -359,6 +359,12 @@ func (h *Handler) doActiveHealthCheckForAllHosts() {
 				dialInfoUpstream = &Upstream{
 					Dial: h.HealthChecks.Active.Upstream,
 				}
+			} else if upstream.activeHealthCheckPort != 0 {
+				// health_port overrides the port; addr has already been updated
+				// with the health port, so use its address for dialing
+				dialInfoUpstream = &Upstream{
+					Dial: addr.JoinHostPort(0),
+				}
 			}
 			dialInfo, _ := dialInfoUpstream.fillDialInfo(repl)

@@ -19,7 +19,9 @@ import (
 	"fmt"
 	"net/netip"
 	"strconv"
+	"sync"
 	"sync/atomic"
+	"time"

 	"github.com/caddyserver/caddy/v2"
 	"github.com/caddyserver/caddy/v2/modules/caddyhttp"
@@ -132,6 +134,43 @@ func (u *Upstream) fillHost() {
 	u.Host = host
 }

+// fillDynamicHost is like fillHost, but stores the host in the separate
+// dynamicHosts map rather than the reference-counted UsagePool. Dynamic
+// hosts are not reference-counted; instead, they are retained as long as
+// they are actively seen and are evicted by a background cleanup goroutine
+// after dynamicHostIdleExpiry of inactivity. This preserves health state
+// (e.g. passive fail counts) across sequential requests.
+func (u *Upstream) fillDynamicHost() {
+	dynamicHostsMu.Lock()
+	entry, ok := dynamicHosts[u.String()]
+	if ok {
+		entry.lastSeen = time.Now()
+		dynamicHosts[u.String()] = entry
+		u.Host = entry.host
+	} else {
+		h := new(Host)
+		dynamicHosts[u.String()] = dynamicHostEntry{host: h, lastSeen: time.Now()}
+		u.Host = h
+	}
+	dynamicHostsMu.Unlock()
+
+	// ensure the cleanup goroutine is running
+	dynamicHostsCleanerOnce.Do(func() {
+		go func() {
+			for {
+				time.Sleep(dynamicHostCleanupInterval)
+				dynamicHostsMu.Lock()
+				for addr, entry := range dynamicHosts {
+					if time.Since(entry.lastSeen) > dynamicHostIdleExpiry {
+						delete(dynamicHosts, addr)
+					}
+				}
+				dynamicHostsMu.Unlock()
+			}
+		}()
+	})
+}
+
 // Host is the basic, in-memory representation of the state of a remote host.
 // Its fields are accessed atomically and Host values must not be copied.
 type Host struct {
@@ -268,6 +307,28 @@ func GetDialInfo(ctx context.Context) (DialInfo, bool) {
 // through config reloads.
 var hosts = caddy.NewUsagePool()

+// dynamicHosts tracks hosts that were provisioned from dynamic upstream
+// sources. Unlike static upstreams which are reference-counted via the
+// UsagePool, dynamic upstream hosts are not reference-counted. Instead,
+// their last-seen time is updated on each request, and a background
+// goroutine evicts entries that have been idle for dynamicHostIdleExpiry.
+// This preserves health state (e.g. passive fail counts) across requests
+// to the same dynamic backend.
+var (
+	dynamicHosts               = make(map[string]dynamicHostEntry)
+	dynamicHostsMu             sync.RWMutex
+	dynamicHostsCleanerOnce    sync.Once
+	dynamicHostCleanupInterval = 5 * time.Minute
+	dynamicHostIdleExpiry      = time.Hour
+)
+
+// dynamicHostEntry holds a Host and the last time it was seen
+// in a set of dynamic upstreams returned for a request.
+type dynamicHostEntry struct {
+	host     *Host
+	lastSeen time.Time
+}
+
 // dialInfoVarKey is the key used for the variable that holds
 // the dial info for the upstream connection.
 const dialInfoVarKey = "reverse_proxy.dial_info"
@@ -384,6 +384,9 @@ func (h *HTTPTransport) NewTransport(caddyCtx caddy.Context) (*http.Transport, e
 	}
 	// we need to keep track if a proxy is used for a request
 	proxyWrapper := func(req *http.Request) (*url.URL, error) {
+		if proxy == nil {
+			return nil, nil
+		}
 		u, err := proxy(req)
 		if u == nil || err != nil {
 			return u, err
@@ -412,8 +415,13 @@ func (h *HTTPTransport) NewTransport(caddyCtx caddy.Context) (*http.Transport, e
 			return nil, fmt.Errorf("making TLS client config: %v", err)
 		}

-		// servername has a placeholder, so we need to replace it
-		if strings.Contains(h.TLS.ServerName, "{") {
+		serverNameHasPlaceholder := strings.Contains(h.TLS.ServerName, "{")
+
+		// We need to use custom DialTLSContext if:
+		// 1. ServerName has a placeholder that needs to be replaced at request-time, OR
+		// 2. ProxyProtocol is enabled, because req.URL.Host is modified to include
+		//    client address info with "->" separator which breaks Go's address parsing
+		if serverNameHasPlaceholder || h.ProxyProtocol != "" {
 			rt.DialTLSContext = func(ctx context.Context, network, addr string) (net.Conn, error) {
 				// reuses the dialer from above to establish a plaintext connection
 				conn, err := dialContext(ctx, network, addr)
@@ -422,9 +430,11 @@ func (h *HTTPTransport) NewTransport(caddyCtx caddy.Context) (*http.Transport, e
 				}

 				// but add our own handshake logic
-				repl := ctx.Value(caddy.ReplacerCtxKey).(*caddy.Replacer)
 				tlsConfig := rt.TLSClientConfig.Clone()
-				tlsConfig.ServerName = repl.ReplaceAll(tlsConfig.ServerName, "")
+				if serverNameHasPlaceholder {
+					repl := ctx.Value(caddy.ReplacerCtxKey).(*caddy.Replacer)
+					tlsConfig.ServerName = repl.ReplaceAll(tlsConfig.ServerName, "")
+				}

 				// h1 only
 				if caddyhttp.GetVar(ctx, tlsH1OnlyVarKey) == true {
@@ -438,7 +448,7 @@ func (h *HTTPTransport) NewTransport(caddyCtx caddy.Context) (*http.Transport, e
 				// complete the handshake before returning the connection
 				if rt.TLSHandshakeTimeout != 0 {
 					var cancel context.CancelFunc
-					ctx, cancel = context.WithTimeout(ctx, rt.TLSHandshakeTimeout)
+					ctx, cancel = context.WithTimeoutCause(ctx, rt.TLSHandshakeTimeout, fmt.Errorf("HTTP transport TLS handshake %ds timeout", int(rt.TLSHandshakeTimeout.Seconds())))
 					defer cancel()
 				}
 				err = tlsConn.HandshakeContext(ctx)
@@ -1,11 +1,13 @@
 package reverseproxy

 import (
+	"context"
 	"encoding/json"
 	"fmt"
 	"reflect"
 	"testing"

+	"github.com/caddyserver/caddy/v2"
 	"github.com/caddyserver/caddy/v2/caddyconfig/caddyfile"
 )

@@ -115,3 +117,81 @@ func TestHTTPTransport_RequestHeaderOps_TLS(t *testing.T) {
 		t.Fatalf("unexpected Host value; want placeholder, got: %s", got)
 	}
 }
+
+// TestHTTPTransport_DialTLSContext_ProxyProtocol verifies that when TLS and
+// ProxyProtocol are both enabled, DialTLSContext is set. This is critical because
+// ProxyProtocol modifies req.URL.Host to include client info with "->" separator
+// (e.g., "[2001:db8::1]:12345->127.0.0.1:443"), which breaks Go's address parsing.
+// Without a custom DialTLSContext, Go's HTTP library would fail with
+// "too many colons in address" when trying to parse the mangled host.
+func TestHTTPTransport_DialTLSContext_ProxyProtocol(t *testing.T) {
+	ctx, cancel := caddy.NewContext(caddy.Context{Context: context.Background()})
+	defer cancel()
+
+	tests := []struct {
+		name                    string
+		tls                     *TLSConfig
+		proxyProtocol           string
+		serverNameHasPlaceholder bool
+		expectDialTLSContext    bool
+	}{
+		{
+			name:                 "no TLS, no proxy protocol",
+			tls:                  nil,
+			proxyProtocol:        "",
+			expectDialTLSContext: false,
+		},
+		{
+			name:                 "TLS without proxy protocol",
+			tls:                  &TLSConfig{},
+			proxyProtocol:        "",
+			expectDialTLSContext: false,
+		},
+		{
+			name:                 "TLS with proxy protocol v1",
+			tls:                  &TLSConfig{},
+			proxyProtocol:        "v1",
+			expectDialTLSContext: true,
+		},
+		{
+			name:                 "TLS with proxy protocol v2",
+			tls:                  &TLSConfig{},
+			proxyProtocol:        "v2",
+			expectDialTLSContext: true,
+		},
+		{
+			name:                     "TLS with placeholder ServerName",
+			tls:                      &TLSConfig{ServerName: "{http.request.host}"},
+			proxyProtocol:            "",
+			serverNameHasPlaceholder: true,
+			expectDialTLSContext:     true,
+		},
+		{
+			name:                     "TLS with placeholder ServerName and proxy protocol",
+			tls:                      &TLSConfig{ServerName: "{http.request.host}"},
+			proxyProtocol:            "v2",
+			serverNameHasPlaceholder: true,
+			expectDialTLSContext:     true,
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			ht := &HTTPTransport{
+				TLS:           tt.tls,
+				ProxyProtocol: tt.proxyProtocol,
+			}
+
+			rt, err := ht.NewTransport(ctx)
+			if err != nil {
+				t.Fatalf("NewTransport() error = %v", err)
+			}
+
+			hasDialTLSContext := rt.DialTLSContext != nil
+			if hasDialTLSContext != tt.expectDialTLSContext {
+				t.Errorf("DialTLSContext set = %v, want %v", hasDialTLSContext, tt.expectDialTLSContext)
+			}
+		})
+	}
+}
+
@@ -0,0 +1,391 @@
+// Copyright 2015 Matthew Holt and The Caddy Authors
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package reverseproxy
+
+import (
+	"context"
+	"testing"
+	"time"
+
+	"github.com/caddyserver/caddy/v2"
+)
+
+// newPassiveHandler builds a minimal Handler with passive health checks
+// configured and a live caddy.Context so the fail-forgetter goroutine can
+// be cancelled cleanly. The caller must call cancel() when done.
+func newPassiveHandler(t *testing.T, maxFails int, failDuration time.Duration) (*Handler, context.CancelFunc) {
+	t.Helper()
+	caddyCtx, cancel := caddy.NewContext(caddy.Context{Context: context.Background()})
+	h := &Handler{
+		ctx: caddyCtx,
+		HealthChecks: &HealthChecks{
+			Passive: &PassiveHealthChecks{
+				MaxFails:     maxFails,
+				FailDuration: caddy.Duration(failDuration),
+			},
+		},
+	}
+	return h, cancel
+}
+
+// provisionedStaticUpstream creates a static upstream, registers it in the
+// UsagePool, and returns a cleanup func that removes it from the pool.
+func provisionedStaticUpstream(t *testing.T, h *Handler, addr string) (*Upstream, func()) {
+	t.Helper()
+	u := &Upstream{Dial: addr}
+	h.provisionUpstream(u, false)
+	return u, func() { _, _ = hosts.Delete(addr) }
+}
+
+// provisionedDynamicUpstream creates a dynamic upstream, registers it in
+// dynamicHosts, and returns a cleanup func that removes it.
+func provisionedDynamicUpstream(t *testing.T, h *Handler, addr string) (*Upstream, func()) {
+	t.Helper()
+	u := &Upstream{Dial: addr}
+	h.provisionUpstream(u, true)
+	return u, func() {
+		dynamicHostsMu.Lock()
+		delete(dynamicHosts, addr)
+		dynamicHostsMu.Unlock()
+	}
+}
+
+// --- countFailure behaviour ---
+
+// TestCountFailureNoopWhenNoHealthChecks verifies that countFailure is a no-op
+// when HealthChecks is nil.
+func TestCountFailureNoopWhenNoHealthChecks(t *testing.T) {
+	resetDynamicHosts()
+	h := &Handler{}
+	u := &Upstream{Dial: "10.1.0.1:80", Host: new(Host)}
+
+	h.countFailure(u)
+
+	if u.Host.Fails() != 0 {
+		t.Errorf("expected 0 fails with no HealthChecks config, got %d", u.Host.Fails())
+	}
+}
+
+// TestCountFailureNoopWhenZeroDuration verifies that countFailure is a no-op
+// when FailDuration is 0 (the zero value disables passive checks).
+func TestCountFailureNoopWhenZeroDuration(t *testing.T) {
+	resetDynamicHosts()
+	caddyCtx, cancel := caddy.NewContext(caddy.Context{Context: context.Background()})
+	defer cancel()
+	h := &Handler{
+		ctx: caddyCtx,
+		HealthChecks: &HealthChecks{
+			Passive: &PassiveHealthChecks{MaxFails: 1, FailDuration: 0},
+		},
+	}
+	u := &Upstream{Dial: "10.1.0.2:80", Host: new(Host)}
+
+	h.countFailure(u)
+
+	if u.Host.Fails() != 0 {
+		t.Errorf("expected 0 fails with zero FailDuration, got %d", u.Host.Fails())
+	}
+}
+
+// TestCountFailureIncrementsCount verifies that countFailure increments the
+// fail count on the upstream's Host.
+func TestCountFailureIncrementsCount(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Minute)
+	defer cancel()
+	u := &Upstream{Dial: "10.1.0.3:80", Host: new(Host)}
+
+	h.countFailure(u)
+
+	if u.Host.Fails() != 1 {
+		t.Errorf("expected 1 fail after countFailure, got %d", u.Host.Fails())
+	}
+}
+
+// TestCountFailureDecrementsAfterDuration verifies that the fail count is
+// decremented back after FailDuration elapses.
+func TestCountFailureDecrementsAfterDuration(t *testing.T) {
+	resetDynamicHosts()
+	const failDuration = 50 * time.Millisecond
+	h, cancel := newPassiveHandler(t, 2, failDuration)
+	defer cancel()
+	u := &Upstream{Dial: "10.1.0.4:80", Host: new(Host)}
+
+	h.countFailure(u)
+	if u.Host.Fails() != 1 {
+		t.Fatalf("expected 1 fail immediately after countFailure, got %d", u.Host.Fails())
+	}
+
+	// Wait long enough for the forgetter goroutine to fire.
+	time.Sleep(3 * failDuration)
+
+	if u.Host.Fails() != 0 {
+		t.Errorf("expected fail count to return to 0 after FailDuration, got %d", u.Host.Fails())
+	}
+}
+
+// TestCountFailureCancelledContextForgets verifies that cancelling the handler
+// context (simulating a config unload) also triggers the forgetter to run,
+// decrementing the fail count.
+func TestCountFailureCancelledContextForgets(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Hour) // very long duration
+	u := &Upstream{Dial: "10.1.0.5:80", Host: new(Host)}
+
+	h.countFailure(u)
+	if u.Host.Fails() != 1 {
+		t.Fatalf("expected 1 fail immediately after countFailure, got %d", u.Host.Fails())
+	}
+
+	// Cancelling the context should cause the forgetter goroutine to exit and
+	// decrement the count.
+	cancel()
+	time.Sleep(50 * time.Millisecond)
+
+	if u.Host.Fails() != 0 {
+		t.Errorf("expected fail count to be decremented after context cancel, got %d", u.Host.Fails())
+	}
+}
+
+// --- static upstream passive health check ---
+
+// TestStaticUpstreamHealthyWithNoFailures verifies that a static upstream with
+// no recorded failures is considered healthy.
+func TestStaticUpstreamHealthyWithNoFailures(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Minute)
+	defer cancel()
+
+	u, cleanup := provisionedStaticUpstream(t, h, "10.2.0.1:80")
+	defer cleanup()
+
+	if !u.Healthy() {
+		t.Error("upstream with no failures should be healthy")
+	}
+}
+
+// TestStaticUpstreamUnhealthyAtMaxFails verifies that a static upstream is
+// marked unhealthy once its fail count reaches MaxFails.
+func TestStaticUpstreamUnhealthyAtMaxFails(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Minute)
+	defer cancel()
+
+	u, cleanup := provisionedStaticUpstream(t, h, "10.2.0.2:80")
+	defer cleanup()
+
+	h.countFailure(u)
+	if !u.Healthy() {
+		t.Error("upstream should still be healthy after 1 of 2 allowed failures")
+	}
+
+	h.countFailure(u)
+	if u.Healthy() {
+		t.Error("upstream should be unhealthy after reaching MaxFails=2")
+	}
+}
+
+// TestStaticUpstreamRecoversAfterFailDuration verifies that a static upstream
+// returns to healthy once its failures expire.
+func TestStaticUpstreamRecoversAfterFailDuration(t *testing.T) {
+	resetDynamicHosts()
+	const failDuration = 50 * time.Millisecond
+	h, cancel := newPassiveHandler(t, 1, failDuration)
+	defer cancel()
+
+	u, cleanup := provisionedStaticUpstream(t, h, "10.2.0.3:80")
+	defer cleanup()
+
+	h.countFailure(u)
+	if u.Healthy() {
+		t.Fatal("upstream should be unhealthy immediately after MaxFails failure")
+	}
+
+	time.Sleep(3 * failDuration)
+
+	if !u.Healthy() {
+		t.Errorf("upstream should recover to healthy after FailDuration, Fails=%d", u.Host.Fails())
+	}
+}
+
+// TestStaticUpstreamHealthPersistedAcrossReprovisioning verifies that static
+// upstreams share a Host via the UsagePool, so a second call to provisionUpstream
+// for the same address (as happens on config reload) sees the accumulated state.
+func TestStaticUpstreamHealthPersistedAcrossReprovisioning(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Minute)
+	defer cancel()
+
+	u1, cleanup1 := provisionedStaticUpstream(t, h, "10.2.0.4:80")
+	defer cleanup1()
+
+	h.countFailure(u1)
+	h.countFailure(u1)
+
+	// Simulate a second handler instance referencing the same upstream
+	// (e.g. after a config reload that keeps the same backend address).
+	u2, cleanup2 := provisionedStaticUpstream(t, h, "10.2.0.4:80")
+	defer cleanup2()
+
+	if u1.Host != u2.Host {
+		t.Fatal("expected both Upstream structs to share the same *Host via UsagePool")
+	}
+	if u2.Healthy() {
+		t.Error("re-provisioned upstream should still see the prior fail count and be unhealthy")
+	}
+}
+
+// --- dynamic upstream passive health check ---
+
+// TestDynamicUpstreamHealthyWithNoFailures verifies that a freshly provisioned
+// dynamic upstream is healthy.
+func TestDynamicUpstreamHealthyWithNoFailures(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Minute)
+	defer cancel()
+
+	u, cleanup := provisionedDynamicUpstream(t, h, "10.3.0.1:80")
+	defer cleanup()
+
+	if !u.Healthy() {
+		t.Error("dynamic upstream with no failures should be healthy")
+	}
+}
+
+// TestDynamicUpstreamUnhealthyAtMaxFails verifies that a dynamic upstream is
+// marked unhealthy once its fail count reaches MaxFails.
+func TestDynamicUpstreamUnhealthyAtMaxFails(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Minute)
+	defer cancel()
+
+	u, cleanup := provisionedDynamicUpstream(t, h, "10.3.0.2:80")
+	defer cleanup()
+
+	h.countFailure(u)
+	if !u.Healthy() {
+		t.Error("dynamic upstream should still be healthy after 1 of 2 allowed failures")
+	}
+
+	h.countFailure(u)
+	if u.Healthy() {
+		t.Error("dynamic upstream should be unhealthy after reaching MaxFails=2")
+	}
+}
+
+// TestDynamicUpstreamFailCountPersistedBetweenRequests is the core regression
+// test: it simulates two sequential (non-concurrent) requests to the same
+// dynamic upstream. Before the fix, the UsagePool entry would be deleted
+// between requests, wiping the fail count. Now it should survive.
+func TestDynamicUpstreamFailCountPersistedBetweenRequests(t *testing.T) {
+	resetDynamicHosts()
+	h, cancel := newPassiveHandler(t, 2, time.Minute)
+	defer cancel()
+
+	// --- first request ---
+	u1 := &Upstream{Dial: "10.3.0.3:80"}
+	h.provisionUpstream(u1, true)
+	h.countFailure(u1)
+
+	if u1.Host.Fails() != 1 {
+		t.Fatalf("expected 1 fail after first request, got %d", u1.Host.Fails())
+	}
+
+	// Simulate end of first request: no delete from any pool (key difference
+	// vs. the old behaviour where hosts.Delete was deferred).
+
+	// --- second request: brand-new *Upstream struct, same dial address ---
+	u2 := &Upstream{Dial: "10.3.0.3:80"}
+	h.provisionUpstream(u2, true)
+
+	if u1.Host != u2.Host {
+		t.Fatal("expected both requests to share the same *Host pointer from dynamicHosts")
+	}
+	if u2.Host.Fails() != 1 {
+		t.Errorf("expected fail count to persist across requests, got %d", u2.Host.Fails())
+	}
+
+	// A second failure now tips it over MaxFails=2.
+	h.countFailure(u2)
+	if u2.Healthy() {
+		t.Error("upstream should be unhealthy after accumulated failures across requests")
+	}
+
+	// Cleanup.
+	dynamicHostsMu.Lock()
+	delete(dynamicHosts, "10.3.0.3:80")
+	dynamicHostsMu.Unlock()
+}
+
+// TestDynamicUpstreamRecoveryAfterFailDuration verifies that a dynamic
+// upstream's fail count expires and it returns to healthy.
+func TestDynamicUpstreamRecoveryAfterFailDuration(t *testing.T) {
+	resetDynamicHosts()
+	const failDuration = 50 * time.Millisecond
+	h, cancel := newPassiveHandler(t, 1, failDuration)
+	defer cancel()
+
+	u, cleanup := provisionedDynamicUpstream(t, h, "10.3.0.4:80")
+	defer cleanup()
+
+	h.countFailure(u)
+	if u.Healthy() {
+		t.Fatal("upstream should be unhealthy immediately after MaxFails failure")
+	}
+
+	time.Sleep(3 * failDuration)
+
+	// Re-provision (as a new request would) to get fresh *Upstream with policy set.
+	u2 := &Upstream{Dial: "10.3.0.4:80"}
+	h.provisionUpstream(u2, true)
+
+	if !u2.Healthy() {
+		t.Errorf("dynamic upstream should recover to healthy after FailDuration, Fails=%d", u2.Host.Fails())
+	}
+}
+
+// TestDynamicUpstreamMaxRequestsFromUnhealthyRequestCount verifies that
+// UnhealthyRequestCount is copied into MaxRequests so Full() works correctly.
+func TestDynamicUpstreamMaxRequestsFromUnhealthyRequestCount(t *testing.T) {
+	resetDynamicHosts()
+	caddyCtx, cancel := caddy.NewContext(caddy.Context{Context: context.Background()})
+	defer cancel()
+	h := &Handler{
+		ctx: caddyCtx,
+		HealthChecks: &HealthChecks{
+			Passive: &PassiveHealthChecks{
+				UnhealthyRequestCount: 3,
+			},
+		},
+	}
+
+	u, cleanup := provisionedDynamicUpstream(t, h, "10.3.0.5:80")
+	defer cleanup()
+
+	if u.MaxRequests != 3 {
+		t.Errorf("expected MaxRequests=3 from UnhealthyRequestCount, got %d", u.MaxRequests)
+	}
+
+	// Should not be full with fewer requests than the limit.
+	_ = u.Host.countRequest(2)
+	if u.Full() {
+		t.Error("upstream should not be full with 2 of 3 allowed requests")
+	}
+
+	_ = u.Host.countRequest(1)
+	if !u.Full() {
+		t.Error("upstream should be full at UnhealthyRequestCount concurrent requests")
+	}
+}
@@ -0,0 +1,257 @@
+package reverseproxy
+
+import (
+	"errors"
+	"io"
+	"net"
+	"net/http"
+	"net/http/httptest"
+	"strings"
+	"sync"
+	"testing"
+
+	"go.uber.org/zap"
+
+	"github.com/caddyserver/caddy/v2"
+	"github.com/caddyserver/caddy/v2/modules/caddyhttp"
+)
+
+// prepareTestRequest injects the context values that ServeHTTP and
+// proxyLoopIteration require (caddy.ReplacerCtxKey, VarsCtxKey, etc.) using
+// the same helper that the real HTTP server uses.
+//
+// A zero-value Server is passed so that caddyhttp.ServerCtxKey is set to a
+// non-nil pointer; reverseProxy dereferences it to check ShouldLogCredentials.
+func prepareTestRequest(req *http.Request) *http.Request {
+	repl := caddy.NewReplacer()
+	return caddyhttp.PrepareRequest(req, repl, nil, &caddyhttp.Server{})
+}
+
+// closeOnCloseReader is an io.ReadCloser whose Close method actually makes
+// subsequent reads fail, mimicking the behaviour of a real HTTP request body
+// (as opposed to io.NopCloser, whose Close is a no-op and would mask the bug
+// we are testing).
+type closeOnCloseReader struct {
+	mu     sync.Mutex
+	r      *strings.Reader
+	closed bool
+}
+
+func newCloseOnCloseReader(s string) *closeOnCloseReader {
+	return &closeOnCloseReader{r: strings.NewReader(s)}
+}
+
+func (c *closeOnCloseReader) Read(p []byte) (int, error) {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	if c.closed {
+		return 0, errors.New("http: invalid Read on closed Body")
+	}
+	return c.r.Read(p)
+}
+
+func (c *closeOnCloseReader) Close() error {
+	c.mu.Lock()
+	defer c.mu.Unlock()
+	c.closed = true
+	return nil
+}
+
+// deadUpstreamAddr returns a TCP address that is guaranteed to refuse
+// connections: we bind a listener, note its address, close it immediately,
+// and return the address. Any dial to that address will get ECONNREFUSED.
+func deadUpstreamAddr(t *testing.T) string {
+	t.Helper()
+	ln, err := net.Listen("tcp", "127.0.0.1:0")
+	if err != nil {
+		t.Fatalf("failed to create dead upstream listener: %v", err)
+	}
+	addr := ln.Addr().String()
+	ln.Close()
+	return addr
+}
+
+// testTransport wraps http.Transport to:
+//  1. Set the URL scheme to "http" when it is empty (matching what
+//     HTTPTransport.SetScheme does in production; cloneRequest strips the
+//     scheme intentionally so a plain *http.Transport would fail with
+//     "unsupported protocol scheme").
+//  2. Wrap dial errors as DialError so that tryAgain correctly identifies them
+//     as safe-to-retry regardless of request method (as HTTPTransport does in
+//     production via its custom dialer).
+type testTransport struct{ *http.Transport }
+
+func (t testTransport) RoundTrip(req *http.Request) (*http.Response, error) {
+	if req.URL.Scheme == "" {
+		req.URL.Scheme = "http"
+	}
+	resp, err := t.Transport.RoundTrip(req)
+	if err != nil {
+		// Wrap dial errors as DialError to match production behaviour.
+		// Without this wrapping, tryAgain treats ECONNREFUSED on a POST
+		// request as non-retryable (only GET is retried by default when
+		// the error is not a DialError).
+		var opErr *net.OpError
+		if errors.As(err, &opErr) && opErr.Op == "dial" {
+			return nil, DialError{err}
+		}
+	}
+	return resp, err
+}
+
+// minimalHandler returns a Handler with only the fields required by ServeHTTP
+// set directly, bypassing Provision (which requires a full Caddy runtime).
+// RoundRobinSelection is used so that successive iterations of the proxy loop
+// advance through the upstream pool in a predictable order.
+func minimalHandler(retries int, upstreams ...*Upstream) *Handler {
+	return &Handler{
+		logger:    zap.NewNop(),
+		Transport: testTransport{&http.Transport{}},
+		Upstreams: upstreams,
+		LoadBalancing: &LoadBalancing{
+			Retries:         retries,
+			SelectionPolicy: &RoundRobinSelection{},
+			// RetryMatch intentionally nil: dial errors are always retried
+			// regardless of RetryMatch or request method.
+		},
+		// ctx, connections, connectionsMu, events: zero/nil values are safe
+		// for the code paths exercised by these tests (TryInterval=0 so
+		// ctx.Done() is never consulted; no WebSocket hijacking; no passive
+		// health-check event emission).
+	}
+}
+
+// TestDialErrorBodyRetry verifies that a POST request whose body has NOT been
+// pre-buffered via request_buffers can still be retried after a dial error.
+//
+// Before the fix, a dial error caused Go's transport to close the shared body
+// (via cloneRequest's shallow copy), so the retry attempt would read from an
+// already-closed io.ReadCloser and produce:
+//
+//	http: invalid Read on closed Body → HTTP 502
+//
+// After the fix the handler wraps the body in noCloseBody when retries are
+// configured, preventing the transport's Close() from propagating to the
+// shared body. Since dial errors never read any bytes, the body remains at
+// position 0 for the retry.
+func TestDialErrorBodyRetry(t *testing.T) {
+	// Good upstream: echoes the request body with 200 OK.
+	goodServer := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		body, err := io.ReadAll(r.Body)
+		if err != nil {
+			http.Error(w, "read body: "+err.Error(), http.StatusInternalServerError)
+			return
+		}
+		w.WriteHeader(http.StatusOK)
+		_, _ = w.Write(body)
+	}))
+	t.Cleanup(goodServer.Close)
+
+	const requestBody = "hello, retry"
+
+	tests := []struct {
+		name       string
+		method     string
+		body       string
+		retries    int
+		wantStatus int
+		wantBody   string
+	}{
+		{
+			// Core regression case: POST with a body, no request_buffers,
+			// dial error on first upstream → retry to second upstream succeeds.
+			name:       "POST body retried after dial error",
+			method:     http.MethodPost,
+			body:       requestBody,
+			retries:    1,
+			wantStatus: http.StatusOK,
+			wantBody:   requestBody,
+		},
+		{
+			// Dial errors are always retried regardless of method, but there
+			// is no body to re-read, so GET has always worked. Keep it as a
+			// sanity check that we did not break the no-body path.
+			name:       "GET without body retried after dial error",
+			method:     http.MethodGet,
+			body:       "",
+			retries:    1,
+			wantStatus: http.StatusOK,
+			wantBody:   "",
+		},
+		{
+			// Without any retry configuration the handler must give up on the
+			// first dial error and return a 502. Confirms no wrapping occurs
+			// in the no-retry path.
+			name:       "no retries configured returns 502 on dial error",
+			method:     http.MethodPost,
+			body:       requestBody,
+			retries:    0,
+			wantStatus: http.StatusBadGateway,
+			wantBody:   "",
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			dead := deadUpstreamAddr(t)
+
+			// Build the upstream pool. RoundRobinSelection starts its
+			// counter at 0 and increments before returning, so with a
+			// two-element pool it picks index 1 first, then index 0.
+			// Put the good upstream at index 0 and the dead one at
+			// index 1 so that:
+			//   attempt 1 → pool[1] = dead → DialError (ECONNREFUSED)
+			//   attempt 2 → pool[0] = good → 200
+			upstreams := []*Upstream{
+				{Host: new(Host), Dial: goodServer.Listener.Addr().String()},
+				{Host: new(Host), Dial: dead},
+			}
+			if tc.retries == 0 {
+				// For the "no retries" case use only the dead upstream so
+				// there is nowhere to retry to.
+				upstreams = []*Upstream{
+					{Host: new(Host), Dial: dead},
+				}
+			}
+
+			h := minimalHandler(tc.retries, upstreams...)
+
+			// Use closeOnCloseReader so that Close() truly prevents further
+			// reads, matching real http.body semantics. io.NopCloser would
+			// mask the bug because its Close is a no-op.
+			var bodyReader io.ReadCloser
+			if tc.body != "" {
+				bodyReader = newCloseOnCloseReader(tc.body)
+			}
+			req := httptest.NewRequest(tc.method, "http://example.com/", bodyReader)
+			if bodyReader != nil {
+				// httptest.NewRequest wraps the reader in NopCloser; replace
+				// it with our close-aware reader so Close() is propagated.
+				req.Body = bodyReader
+				req.ContentLength = int64(len(tc.body))
+			}
+			req = prepareTestRequest(req)
+
+			rec := httptest.NewRecorder()
+			err := h.ServeHTTP(rec, req, caddyhttp.HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
+				return nil
+			}))
+
+			// For error cases (e.g. 502) ServeHTTP returns a HandlerError
+			// rather than writing the status itself.
+			gotStatus := rec.Code
+			if err != nil {
+				if herr, ok := err.(caddyhttp.HandlerError); ok {
+					gotStatus = herr.StatusCode
+				}
+			}
+
+			if gotStatus != tc.wantStatus {
+				t.Errorf("status: got %d, want %d (err=%v)", gotStatus, tc.wantStatus, err)
+			}
+			if tc.wantBody != "" && rec.Body.String() != tc.wantBody {
+				t.Errorf("body: got %q, want %q", rec.Body.String(), tc.wantBody)
+			}
+		})
+	}
+}
@@ -32,6 +32,7 @@ import (
 	"strconv"
 	"strings"
 	"sync"
+	"sync/atomic"
 	"time"

 	"go.uber.org/zap"
@@ -46,6 +47,31 @@ import (
 	"github.com/caddyserver/caddy/v2/modules/caddyhttp/rewrite"
 )

+// inFlightRequests uses sync.Map with atomic.Int64 for lock-free updates on the hot path
+var inFlightRequests sync.Map
+
+func incInFlightRequest(address string) {
+	v, _ := inFlightRequests.LoadOrStore(address, new(atomic.Int64))
+	v.(*atomic.Int64).Add(1)
+}
+
+func decInFlightRequest(address string) {
+	if v, ok := inFlightRequests.Load(address); ok {
+		if v.(*atomic.Int64).Add(-1) <= 0 {
+			inFlightRequests.Delete(address)
+		}
+	}
+}
+
+func getInFlightRequests() map[string]int64 {
+	copyMap := make(map[string]int64)
+	inFlightRequests.Range(func(key, value any) bool {
+		copyMap[key.(string)] = value.(*atomic.Int64).Load()
+		return true
+	})
+	return copyMap
+}
+
 func init() {
 	caddy.RegisterModule(Handler{})
 }
@@ -366,7 +392,7 @@ func (h *Handler) Provision(ctx caddy.Context) error {

 	// set up upstreams
 	for _, u := range h.Upstreams {
-		h.provisionUpstream(u)
+		h.provisionUpstream(u, false)
 	}

 	if h.HealthChecks != nil {
@@ -456,18 +482,31 @@ func (h *Handler) ServeHTTP(w http.ResponseWriter, r *http.Request, next caddyht
 	reqHost := clonedReq.Host
 	reqHeader := clonedReq.Header

-	// If the cloned request body was fully buffered, keep a reference to its
-	// buffer so we can reuse it across retries and return it to the pool
-	// once we’re done.
+	// When retries are configured and there is a body, wrap it in
+	// io.NopCloser to prevent Go's transport from closing it on dial
+	// errors. cloneRequest does a shallow copy, so clonedReq.Body and
+	// r.Body share the same io.ReadCloser — a dial-failure Close()
+	// would kill the original body for all subsequent retry attempts.
+	// The real body is closed by the HTTP server when the handler
+	// returns.
+	//
+	// If the body was already fully buffered (via request_buffers),
+	// we also extract the buffer so the retry loop can replay it
+	// from the beginning on each attempt. (see #6259, #7546)
 	var bufferedReqBody *bytes.Buffer
-	if reqBodyBuf, ok := clonedReq.Body.(bodyReadCloser); ok && reqBodyBuf.body == nil && reqBodyBuf.buf != nil {
-		bufferedReqBody = reqBodyBuf.buf
-		reqBodyBuf.buf = nil
-
-		defer func() {
-			bufferedReqBody.Reset()
-			bufPool.Put(bufferedReqBody)
-		}()
+	if clonedReq.Body != nil && h.LoadBalancing != nil &&
+		(h.LoadBalancing.Retries > 0 || h.LoadBalancing.TryDuration > 0) {
+		if reqBodyBuf, ok := clonedReq.Body.(bodyReadCloser); ok && reqBodyBuf.body == nil && reqBodyBuf.buf != nil {
+			bufferedReqBody = reqBodyBuf.buf
+			reqBodyBuf.buf = nil
+			clonedReq.Body = io.NopCloser(bytes.NewReader(bufferedReqBody.Bytes()))
+			defer func() {
+				bufferedReqBody.Reset()
+				bufPool.Put(bufferedReqBody)
+			}()
+		} else {
+			clonedReq.Body = io.NopCloser(clonedReq.Body)
+		}
 	}

 	start := time.Now()
@@ -537,18 +576,11 @@ func (h *Handler) proxyLoopIteration(r *http.Request, origReq *http.Request, w h
 		} else {
 			upstreams = dUpstreams
 			for _, dUp := range dUpstreams {
-				h.provisionUpstream(dUp)
+				h.provisionUpstream(dUp, true)
 			}
 			if c := h.logger.Check(zapcore.DebugLevel, "provisioned dynamic upstreams"); c != nil {
 				c.Write(zap.Int("count", len(dUpstreams)))
 			}
-			defer func() {
-				// these upstreams are dynamic, so they are only used for this iteration
-				// of the proxy loop; be sure to let them go away when we're done with them
-				for _, upstream := range dUpstreams {
-					_, _ = hosts.Delete(upstream.String())
-				}
-			}()
 		}
 	}

@@ -904,8 +936,16 @@ func (h Handler) addForwardedHeaders(req *http.Request) error {
 // Go standard library which was used as the foundation.)
 func (h *Handler) reverseProxy(rw http.ResponseWriter, req *http.Request, origReq *http.Request, repl *caddy.Replacer, di DialInfo, next caddyhttp.Handler) error {
 	_ = di.Upstream.Host.countRequest(1)
+
+	// Increment the in-flight request count
+	incInFlightRequest(di.Address)
+
 	//nolint:errcheck
-	defer di.Upstream.Host.countRequest(-1)
+	defer func() {
+		di.Upstream.Host.countRequest(-1)
+		// Decrement the in-flight request count
+		decInFlightRequest(di.Address)
+	}()

 	// point the request to this upstream
 	h.directRequest(req, di)
@@ -1278,16 +1318,28 @@ func (h *Handler) directRequest(req *http.Request, di DialInfo) {
 	// add client address to the host to let transport differentiate requests from different clients
 	if ppt, ok := h.Transport.(ProxyProtocolTransport); ok && ppt.ProxyProtocolEnabled() {
 		if proxyProtocolInfo, ok := caddyhttp.GetVar(req.Context(), proxyProtocolInfoVarKey).(ProxyProtocolInfo); ok {
-			reqHost = proxyProtocolInfo.AddrPort.String() + "->" + reqHost
+			// encode the request so it plays well with h2 transport, it's unnecessary for h1 but anyway
+			// The issue is that h2 transport will use the address to determine if new connections are needed
+			// to roundtrip requests but the without escaping, new connections are constantly created and closed until
+			// file descriptors are exhausted.
+			// see: https://github.com/caddyserver/caddy/issues/7529
+			reqHost = url.QueryEscape(proxyProtocolInfo.AddrPort.String() + "->" + reqHost)
 		}
 	}

 	req.URL.Host = reqHost
 }

-func (h Handler) provisionUpstream(upstream *Upstream) {
-	// create or get the host representation for this upstream
-	upstream.fillHost()
+func (h Handler) provisionUpstream(upstream *Upstream, dynamic bool) {
+	// create or get the host representation for this upstream;
+	// dynamic upstreams are tracked in a separate map with last-seen
+	// timestamps so their health state persists across requests without
+	// being reference-counted (and thus discarded between requests).
+	if dynamic {
+		upstream.fillDynamicHost()
+	} else {
+		upstream.fillHost()
+	}

 	// give it the circuit breaker, if any
 	upstream.cb = h.CB
@@ -312,7 +312,7 @@ func (r *RoundRobinSelection) Select(pool UpstreamPool, _ *http.Request, _ http.
 	if n == 0 {
 		return nil
 	}
-	for i := uint32(0); i < n; i++ {
+	for range n {
 		robin := atomic.AddUint32(&r.robin, 1)
 		host := pool[robin%n]
 		if host.Available() {
@@ -536,7 +536,7 @@ func maskBytes(key [4]byte, pos int, b []byte) int {
 	// Mask one word at a time.
 	n := (len(b) / wordSize) * wordSize
 	for i := 0; i < n; i += wordSize {
-		*(*uintptr)(unsafe.Pointer(uintptr(unsafe.Pointer(&b[0])) + uintptr(i))) ^= kw
+		*(*uintptr)(unsafe.Add(unsafe.Pointer(&b[0]), i)) ^= kw
 	}

 	// Mask one byte at a time for remaining bytes.
@@ -247,6 +247,7 @@ func (rewr Rewrite) Rewrite(r *http.Request, repl *caddy.Replacer) bool {
 			} else {
 				r.URL.Path = path
 			}
+			r.URL.RawPath = "" // force recomputing when EscapedPath() is called
 		}
 		if qsStart >= 0 {
 			r.URL.RawQuery = newQuery
@@ -224,6 +224,11 @@ func TestRewrite(t *testing.T) {
 			input:  newRequest(t, "GET", "/foo#fragFirst?c=d"),
 			expect: newRequest(t, "GET", "/bar#fragFirst?c=d"),
 		},
+		{
+			rule:   Rewrite{URI: "/api/admin/panel"},
+			input:  newRequest(t, "GET", "/api/admin%2Fpanel"),
+			expect: newRequest(t, "GET", "/api/admin/panel"),
+		},

 		{
 			rule:   Rewrite{StripPathPrefix: "/prefix"},
@@ -97,7 +97,10 @@ type Route struct {
 	MatcherSets MatcherSets         `json:"-"`
 	Handlers    []MiddlewareHandler `json:"-"`

-	middleware []Middleware
+	middleware  []Middleware
+	metrics     *Metrics
+	metricsCtx  caddy.Context
+	handlerName string
 }

 // Empty returns true if the route has all zero/default values.
@@ -162,12 +165,20 @@ func (r *Route) ProvisionHandlers(ctx caddy.Context, metrics *Metrics) error {
 		r.Handlers = append(r.Handlers, handler.(MiddlewareHandler))
 	}

+	// Store metrics info for route-level instrumentation (applied once
+	// per route in wrapRoute, instead of per-handler which was redundant).
+	r.metrics = metrics
+	r.metricsCtx = ctx
+	if len(r.Handlers) > 0 {
+		r.handlerName = caddy.GetModuleName(r.Handlers[0])
+	}
+
 	// Make ProvisionHandlers idempotent by clearing the middleware field
 	r.middleware = []Middleware{}

 	// pre-compile the middleware handler chain
 	for _, midhandler := range r.Handlers {
-		r.middleware = append(r.middleware, wrapMiddleware(ctx, midhandler, metrics))
+		r.middleware = append(r.middleware, wrapMiddleware(ctx, midhandler))
 	}
 	return nil
 }
@@ -298,6 +309,16 @@ func wrapRoute(route Route) Middleware {
 				nextCopy = route.middleware[i](nextCopy)
 			}

+			// Apply metrics instrumentation once for the entire route,
+			// rather than wrapping each individual handler. This avoids
+			// redundant metrics collection that caused significant CPU
+			// overhead (see issue #4644).
+			if route.metrics != nil {
+				nextCopy = newMetricsInstrumentedRoute(
+					route.metricsCtx, route.handlerName, nextCopy, route.metrics,
+				)
+			}
+
 			return nextCopy.ServeHTTP(rw, req)
 		})
 	}
@@ -306,20 +327,14 @@ func wrapRoute(route Route) Middleware {
 // wrapMiddleware wraps mh such that it can be correctly
 // appended to a list of middleware in preparation for
 // compiling into a handler chain.
-func wrapMiddleware(ctx caddy.Context, mh MiddlewareHandler, metrics *Metrics) Middleware {
-	handlerToUse := mh
-	if metrics != nil {
-		// wrap the middleware with metrics instrumentation
-		handlerToUse = newMetricsInstrumentedHandler(ctx, caddy.GetModuleName(mh), mh, metrics)
-	}
-
+func wrapMiddleware(ctx caddy.Context, mh MiddlewareHandler) Middleware {
 	return func(next Handler) Handler {
 		return HandlerFunc(func(w http.ResponseWriter, r *http.Request) error {
 			// EXPERIMENTAL: Trace each module that gets invoked
 			if server, ok := r.Context().Value(ServerCtxKey).(*Server); ok && server != nil {
-				server.logTrace(handlerToUse)
+				server.logTrace(mh)
 			}
-			return handlerToUse.ServeHTTP(w, r, next)
+			return mh.ServeHTTP(w, r, next)
 		})
 	}
 }
@@ -486,7 +486,7 @@ func (s *Server) serveHTTP(w http.ResponseWriter, r *http.Request) error {
 	// code to any HTTP/1.1 request message that lacks a Host header field and to any
 	// request message that contains more than one Host header field line or a Host
 	// header field with an invalid field value."
-	if r.Host == "" {
+	if r.ProtoMajor == 1 && r.ProtoMinor == 1 && r.Host == "" {
 		return HandlerError{
 			Err:        errors.New("rfc9112 forbids empty Host"),
 			StatusCode: http.StatusBadRequest,
@@ -312,10 +312,12 @@ func (m MatchVarsRE) MatchWithError(r *http.Request) (bool, error) {
 	repl := r.Context().Value(caddy.ReplacerCtxKey).(*caddy.Replacer)
 	for key, val := range m {
 		var varValue any
+		var fromPlaceholder bool
 		if strings.HasPrefix(key, "{") &&
 			strings.HasSuffix(key, "}") &&
 			strings.Count(key, "{") == 1 {
 			varValue, _ = repl.Get(strings.Trim(key, "{}"))
+			fromPlaceholder = true
 		} else {
 			varValue = vars[key]
 		}
@@ -334,7 +336,14 @@ func (m MatchVarsRE) MatchWithError(r *http.Request) (bool, error) {
 			varStr = fmt.Sprintf("%v", vv)
 		}

-		valExpanded := repl.ReplaceAll(varStr, "")
+		// Only expand placeholders in values from literal variable names
+		// (e.g. map outputs). Values resolved from placeholder keys are
+		// already final and must not be re-expanded, as that would allow
+		// user input like {env.SECRET} to be evaluated.
+		valExpanded := varStr
+		if !fromPlaceholder {
+			valExpanded = repl.ReplaceAll(varStr, "")
+		}
 		if match := val.Match(valExpanded, repl); match {
 			return match, nil
 		}
@@ -40,6 +40,7 @@ import (
 	"github.com/caddyserver/caddy/v2"
 	"github.com/caddyserver/caddy/v2/modules/caddyhttp"
 	"github.com/caddyserver/caddy/v2/modules/caddypki"
+	"github.com/caddyserver/caddy/v2/modules/caddytls"
 )

 func init() {
@@ -304,7 +305,19 @@ func (ash Handler) openDatabase() (*db.AuthDB, error) {
 // makeClient creates an ACME client which will use a custom
 // resolver instead of net.DefaultResolver.
 func (ash Handler) makeClient() (acme.Client, error) {
-	for _, v := range ash.Resolvers {
+	// If no local resolvers are configured, check for global resolvers from TLS app
+	resolversToUse := ash.Resolvers
+	if len(resolversToUse) == 0 {
+		tlsAppIface, err := ash.ctx.App("tls")
+		if err == nil {
+			tlsApp := tlsAppIface.(*caddytls.TLS)
+			if len(tlsApp.Resolvers) > 0 {
+				resolversToUse = tlsApp.Resolvers
+			}
+		}
+	}
+
+	for _, v := range resolversToUse {
 		addr, err := caddy.ParseNetworkAddressWithDefaults(v, "udp", 53)
 		if err != nil {
 			return nil, err
@@ -243,22 +243,49 @@ func (ap *AutomationPolicy) Provision(tlsApp *TLS) error {
 		}
 	}

+	// build certmagic.Config and attach it to the policy
+	storage := ap.storage
+	if storage == nil {
+		storage = tlsApp.ctx.Storage()
+	}
+	cfg, err := ap.makeCertMagicConfig(tlsApp, issuers, storage)
+	if err != nil {
+		return err
+	}
+	certCacheMu.RLock()
+	ap.magic = certmagic.New(certCache, cfg)
+	certCacheMu.RUnlock()
+
+	// give issuers a chance to see the config pointer
+	for _, issuer := range ap.magic.Issuers {
+		if annoying, ok := issuer.(ConfigSetter); ok {
+			annoying.SetConfig(ap.magic)
+		}
+	}
+
+	return nil
+}
+
+// makeCertMagicConfig constructs a certmagic.Config for this policy using the
+// provided issuers and storage. It encapsulates common logic shared between
+// Provision and RebuildCertMagic so we don't duplicate code.
+func (ap *AutomationPolicy) makeCertMagicConfig(tlsApp *TLS, issuers []certmagic.Issuer, storage certmagic.Storage) (certmagic.Config, error) {
+	// key source
 	keyType := ap.KeyType
 	if keyType != "" {
 		var err error
 		keyType, err = caddy.NewReplacer().ReplaceOrErr(ap.KeyType, true, true)
 		if err != nil {
-			return fmt.Errorf("invalid key type %s: %s", ap.KeyType, err)
+			return certmagic.Config{}, fmt.Errorf("invalid key type %s: %s", ap.KeyType, err)
 		}
 		if _, ok := supportedCertKeyTypes[keyType]; !ok {
-			return fmt.Errorf("unrecognized key type: %s", keyType)
+			return certmagic.Config{}, fmt.Errorf("unrecognized key type: %s", keyType)
 		}
 	}
 	keySource := certmagic.StandardKeyGenerator{
 		KeyType: supportedCertKeyTypes[keyType],
 	}

-	storage := ap.storage
 	if storage == nil {
 		storage = tlsApp.ctx.Storage()
 	}
@@ -277,7 +304,7 @@ func (ap *AutomationPolicy) Provision(tlsApp *TLS) error {
 		if noProtections {
 			if !ap.hadExplicitManagers {
 				// no managers, no explicitly-configured permission module, this is a config error
-				return fmt.Errorf("on-demand TLS cannot be enabled without a permission module to prevent abuse; please refer to documentation for details")
+				return certmagic.Config{}, fmt.Errorf("on-demand TLS cannot be enabled without a permission module to prevent abuse; please refer to documentation for details")
 			}
 			// allow on-demand to be enabled but only for the purpose of the Managers; issuance won't be allowed from Issuers
 			tlsApp.logger.Warn("on-demand TLS can only get certificates from the configured external manager(s) because no ask endpoint / permission module is specified")
@@ -334,7 +361,7 @@ func (ap *AutomationPolicy) Provision(tlsApp *TLS) error {
 		}
 	}

-	template := certmagic.Config{
+	cfg := certmagic.Config{
 		MustStaple:         ap.MustStaple,
 		RenewalWindowRatio: ap.RenewalWindowRatio,
 		KeySource:          keySource,
@@ -349,8 +376,31 @@ func (ap *AutomationPolicy) Provision(tlsApp *TLS) error {
 		Issuers: issuers,
 		Logger:  tlsApp.logger,
 	}
+
+	return cfg, nil
+}
+
+// IsProvisioned reports whether the automation policy has been
+// provisioned. A provisioned policy has an initialized CertMagic
+// instance (i.e. ap.magic != nil).
+func (ap *AutomationPolicy) IsProvisioned() bool { return ap.magic != nil }
+
+// RebuildCertMagic rebuilds the policy's CertMagic configuration from the
+// policy's already-populated fields (Issuers, Managers, storage, etc.) and
+// replaces the internal CertMagic instance. This is a lightweight
+// alternative to calling Provision because it does not re-provision
+// modules or re-run module Provision; instead, it constructs a new
+// certmagic.Config and calls SetConfig on issuers so they receive updated
+// templates (for example, alternate HTTP/TLS ports supplied by the HTTP
+// app). RebuildCertMagic should only be called when the policy's required
+// fields are already populated.
+func (ap *AutomationPolicy) RebuildCertMagic(tlsApp *TLS) error {
+	cfg, err := ap.makeCertMagicConfig(tlsApp, ap.Issuers, ap.storage)
+	if err != nil {
+		return err
+	}
 	certCacheMu.RLock()
-	ap.magic = certmagic.New(certCache, template)
+	ap.magic = certmagic.New(certCache, cfg)
 	certCacheMu.RUnlock()

 	// sometimes issuers may need the parent certmagic.Config in
@@ -123,8 +123,15 @@ type TLS struct {
 	//
 	// EXPERIMENTAL: Subject to change.
 	DNSRaw json.RawMessage `json:"dns,omitempty" caddy:"namespace=dns.providers inline_key=name"`
-	dns    any             // technically, it should be any/all of the libdns interfaces (RecordSetter, RecordAppender, etc.)

+	// The default DNS resolvers to use for TLS-related DNS operations, specifically
+	// for ACME DNS challenges and ACME server DNS validations.
+	// If not specified, the system default resolvers will be used.
+	//
+	// EXPERIMENTAL: Subject to change.
+	Resolvers []string `json:"resolvers,omitempty"`
+
+	dns                any // technically, it should be any/all of the libdns interfaces (RecordSetter, RecordAppender, etc.)
 	certificateLoaders []CertificateLoader
 	automateNames      map[string]struct{}
 	ctx                caddy.Context
@@ -63,7 +63,7 @@ func (m *fileMode) UnmarshalJSON(b []byte) error {

 // MarshalJSON satisfies json.Marshaler.
 func (m *fileMode) MarshalJSON() ([]byte, error) {
-	return []byte(fmt.Sprintf("\"%04o\"", *m)), nil
+	return fmt.Appendf(nil, "\"%04o\"", *m), nil
 }

 // parseFileMode parses a file mode string,
@@ -90,6 +90,15 @@ type FileWriter struct {
 	// 0600 by default.
 	Mode fileMode `json:"mode,omitempty"`

+	// DirMode controls permissions for any directories created to reach Filename.
+	// Default: 0700 (current behavior).
+	//
+	// Special values:
+	//   - "inherit"   → copy the nearest existing parent directory's perms (with r→x normalization)
+	//   - "from_file" → derive from the file Mode (with r→x), e.g. 0644 → 0755, 0600 → 0700
+	// Numeric octal strings (e.g. "0755") are also accepted. Subject to process umask.
+	DirMode string `json:"dir_mode,omitempty"`
+
 	// Roll toggles log rolling or rotation, which is
 	// enabled by default.
 	Roll *bool `json:"roll,omitempty"`
@@ -113,9 +122,16 @@ type FileWriter struct {
 	// See https://github.com/DeRuina/timberjack#%EF%B8%8F-rotation-notes--warnings for caveats
 	RollAt []string `json:"roll_at,omitempty"`

-	// Whether to compress rolled files. Default: true
+	// Whether to compress rolled files.
+	// Default: true.
+	// Deprecated: Use RollCompression instead, setting it to "none".
 	RollCompress *bool `json:"roll_gzip,omitempty"`

+	// RollCompression selects the compression algorithm for rolled files.
+	// Accepted values: "none", "gzip", "zstd".
+	// Default: gzip
+	RollCompression string `json:"roll_compression,omitempty"`
+
 	// Whether to use local timestamps in rolled filenames.
 	// Default: false
 	RollLocalTime bool `json:"roll_local_time,omitempty"`
@@ -177,11 +193,33 @@ func (fw FileWriter) OpenWriter() (io.WriteCloser, error) {
 	// roll log files as a sensible default to avoid disk space exhaustion
 	roll := fw.Roll == nil || *fw.Roll

-	// create the file if it does not exist; create with the configured mode, or default
-	// to restrictive if not set. (timberjack will reuse the file mode across log rotation)
-	if err := os.MkdirAll(filepath.Dir(fw.Filename), 0o700); err != nil {
-		return nil, err
+	// Ensure directory exists before opening the file.
+	dirPath := filepath.Dir(fw.Filename)
+	switch strings.ToLower(strings.TrimSpace(fw.DirMode)) {
+	case "", "0":
+		// Preserve current behavior: locked-down directories by default.
+		if err := os.MkdirAll(dirPath, 0o700); err != nil {
+			return nil, err
+		}
+	case "inherit":
+		if err := mkdirAllInherit(dirPath); err != nil {
+			return nil, err
+		}
+	case "from_file":
+		if err := mkdirAllFromFile(dirPath, os.FileMode(fw.Mode)); err != nil {
+			return nil, err
+		}
+	default:
+		dm, err := parseFileMode(fw.DirMode)
+		if err != nil {
+			return nil, fmt.Errorf("dir_mode: %w", err)
+		}
+		if err := os.MkdirAll(dirPath, dm); err != nil {
+			return nil, err
+		}
 	}
+
+	// create/open the file
 	file, err := os.OpenFile(fw.Filename, os.O_WRONLY|os.O_APPEND|os.O_CREATE, modeIfCreating)
 	if err != nil {
 		return nil, err
@@ -223,27 +261,104 @@ func (fw FileWriter) OpenWriter() (io.WriteCloser, error) {
 	if fw.RollKeepDays == 0 {
 		fw.RollKeepDays = 90
 	}
+
+	// Determine compression algorithm to use. Priority:
+	// 1) explicit RollCompression (none|gzip|zstd)
+	// 2) if RollCompress is unset or true -> gzip
+	// 3) if RollCompress is false -> none
+	var compression string
+	if fw.RollCompression != "" {
+		compression = strings.ToLower(strings.TrimSpace(fw.RollCompression))
+		if compression != "none" && compression != "gzip" && compression != "zstd" {
+			return nil, fmt.Errorf("invalid roll_compression: %s", fw.RollCompression)
+		}
+	} else {
+		if fw.RollCompress == nil || *fw.RollCompress {
+			compression = "gzip"
+		} else {
+			compression = "none"
+		}
+	}
+
 	return &timberjack.Logger{
 		Filename:         fw.Filename,
 		MaxSize:          fw.RollSizeMB,
 		MaxAge:           fw.RollKeepDays,
 		MaxBackups:       fw.RollKeep,
 		LocalTime:        fw.RollLocalTime,
-		Compress:         *fw.RollCompress,
+		Compression:      compression,
 		RotationInterval: fw.RollInterval,
 		RotateAtMinutes:  fw.RollAtMinutes,
 		RotateAt:         fw.RollAt,
 		BackupTimeFormat: fw.BackupTimeFormat,
+		FileMode:         os.FileMode(fw.Mode),
 	}, nil
 }

+// normalizeDirPerm ensures that read bits also have execute bits set.
+func normalizeDirPerm(p os.FileMode) os.FileMode {
+	if p&0o400 != 0 {
+		p |= 0o100
+	}
+	if p&0o040 != 0 {
+		p |= 0o010
+	}
+	if p&0o004 != 0 {
+		p |= 0o001
+	}
+	return p
+}
+
+// mkdirAllInherit creates missing dirs using the nearest existing parent's
+// permissions, normalized with r→x.
+func mkdirAllInherit(dir string) error {
+	if fi, err := os.Stat(dir); err == nil && fi.IsDir() {
+		return nil
+	}
+	cur := dir
+	var parent string
+	for {
+		next := filepath.Dir(cur)
+		if next == cur {
+			parent = next
+			break
+		}
+		if fi, err := os.Stat(next); err == nil {
+			if !fi.IsDir() {
+				return fmt.Errorf("path component %s exists and is not a directory", next)
+			}
+			parent = next
+			break
+		}
+		cur = next
+	}
+	perm := os.FileMode(0o700)
+	if fi, err := os.Stat(parent); err == nil && fi.IsDir() {
+		perm = fi.Mode().Perm()
+	}
+	perm = normalizeDirPerm(perm)
+	return os.MkdirAll(dir, perm)
+}
+
+// mkdirAllFromFile creates missing dirs using the file's mode (with r→x) so
+// 0644 → 0755, 0600 → 0700, etc.
+func mkdirAllFromFile(dir string, fileMode os.FileMode) error {
+	if fi, err := os.Stat(dir); err == nil && fi.IsDir() {
+		return nil
+	}
+	perm := normalizeDirPerm(fileMode.Perm()) | 0o200 // ensure owner write on dir so files can be created
+	return os.MkdirAll(dir, perm)
+}
+
 // UnmarshalCaddyfile sets up the module from Caddyfile tokens. Syntax:
 //
 //	file <filename> {
 //	    mode          <mode>
+//	    dir_mode      <mode|inherit|from_file>
 //	    roll_disabled
 //	    roll_size     <size>
 //	    roll_uncompressed
+//	    roll_compression <none|gzip|zstd>
 //	    roll_local_time
 //	    roll_keep     <num>
 //	    roll_keep_for <days>
@@ -284,6 +399,22 @@ func (fw *FileWriter) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 			}
 			fw.Mode = fileMode(mode)

+		case "dir_mode":
+			var val string
+			if !d.AllArgs(&val) {
+				return d.ArgErr()
+			}
+			val = strings.TrimSpace(val)
+			switch strings.ToLower(val) {
+			case "inherit", "from_file":
+				fw.DirMode = val
+			default:
+				if _, err := parseFileMode(val); err != nil {
+					return d.Errf("parsing dir_mode: %v", err)
+				}
+				fw.DirMode = val
+			}
+
 		case "roll_disabled":
 			var f bool
 			fw.Roll = &f
@@ -309,6 +440,19 @@ func (fw *FileWriter) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 				return d.ArgErr()
 			}

+		case "roll_compression":
+			var comp string
+			if !d.AllArgs(&comp) {
+				return d.ArgErr()
+			}
+			comp = strings.ToLower(strings.TrimSpace(comp))
+			switch comp {
+			case "none", "gzip", "zstd":
+				fw.RollCompression = comp
+			default:
+				return d.Errf("parsing roll_compression: must be 'none', 'gzip' or 'zstd'")
+			}
+
 		case "roll_local_time":
 			fw.RollLocalTime = true
 			if d.NextArg() {
@@ -352,31 +496,48 @@ func (fw *FileWriter) UnmarshalCaddyfile(d *caddyfile.Dispenser) error {
 			fw.RollInterval = duration

 		case "roll_minutes":
-			var minutesArrayStr string
-			if !d.AllArgs(&minutesArrayStr) {
+			// Accept either a single comma-separated argument or
+			// multiple space-separated arguments. Collect all
+			// remaining args on the line and split on commas.
+			args := d.RemainingArgs()
+			if len(args) == 0 {
 				return d.ArgErr()
 			}
-			minutesStr := strings.Split(minutesArrayStr, ",")
-			minutes := make([]int, len(minutesStr))
-			for i := range minutesStr {
-				ms := strings.Trim(minutesStr[i], " ")
-				m, err := strconv.Atoi(ms)
-				if err != nil {
-					return d.Errf("parsing roll_minutes number: %v", err)
+			var minutes []int
+			for _, arg := range args {
+				parts := strings.SplitSeq(arg, ",")
+				for p := range parts {
+					ms := strings.TrimSpace(p)
+					if ms == "" {
+						return d.Errf("parsing roll_minutes: empty value")
+					}
+					m, err := strconv.Atoi(ms)
+					if err != nil {
+						return d.Errf("parsing roll_minutes number: %v", err)
+					}
+					minutes = append(minutes, m)
 				}
-				minutes[i] = m
 			}
 			fw.RollAtMinutes = minutes

 		case "roll_at":
-			var timeArrayStr string
-			if !d.AllArgs(&timeArrayStr) {
+			// Accept either a single comma-separated argument or
+			// multiple space-separated arguments. Collect all
+			// remaining args on the line and split on commas.
+			args := d.RemainingArgs()
+			if len(args) == 0 {
 				return d.ArgErr()
 			}
-			timeStr := strings.Split(timeArrayStr, ",")
-			times := make([]string, len(timeStr))
-			for i := range timeStr {
-				times[i] = strings.Trim(timeStr[i], " ")
+			var times []string
+			for _, arg := range args {
+				parts := strings.SplitSeq(arg, ",")
+				for p := range parts {
+					ts := strings.TrimSpace(p)
+					if ts == "" {
+						return d.Errf("parsing roll_at: empty value")
+					}
+					times = append(times, ts)
+				}
 			}
 			fw.RollAt = times

@@ -385,3 +385,225 @@ func TestFileModeModification(t *testing.T) {
 		t.Errorf("file mode is %v, want %v", st.Mode(), want)
 	}
 }
+
+func TestDirMode_Inherit(t *testing.T) {
+	m := syscall.Umask(0)
+	defer syscall.Umask(m)
+
+	parent := t.TempDir()
+	if err := os.Chmod(parent, 0o755); err != nil {
+		t.Fatal(err)
+	}
+
+	targetDir := filepath.Join(parent, "a", "b")
+	fw := &FileWriter{
+		Filename: filepath.Join(targetDir, "test.log"),
+		DirMode:  "inherit",
+		Mode:     0o640,
+		Roll:     func() *bool { f := false; return &f }(),
+	}
+	w, err := fw.OpenWriter()
+	if err != nil {
+		t.Fatal(err)
+	}
+	_ = w.Close()
+
+	st, err := os.Stat(targetDir)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got := st.Mode().Perm(); got != 0o755 {
+		t.Fatalf("dir perm = %o, want 0755", got)
+	}
+}
+
+func TestDirMode_FromFile(t *testing.T) {
+	m := syscall.Umask(0)
+	defer syscall.Umask(m)
+
+	base := t.TempDir()
+
+	dir1 := filepath.Join(base, "logs1")
+	fw1 := &FileWriter{
+		Filename: filepath.Join(dir1, "app.log"),
+		DirMode:  "from_file",
+		Mode:     0o644, // => dir 0755
+		Roll:     func() *bool { f := false; return &f }(),
+	}
+	w1, err := fw1.OpenWriter()
+	if err != nil {
+		t.Fatal(err)
+	}
+	_ = w1.Close()
+
+	st1, err := os.Stat(dir1)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got := st1.Mode().Perm(); got != 0o755 {
+		t.Fatalf("dir perm = %o, want 0755", got)
+	}
+
+	dir2 := filepath.Join(base, "logs2")
+	fw2 := &FileWriter{
+		Filename: filepath.Join(dir2, "app.log"),
+		DirMode:  "from_file",
+		Mode:     0o600, // => dir 0700
+		Roll:     func() *bool { f := false; return &f }(),
+	}
+	w2, err := fw2.OpenWriter()
+	if err != nil {
+		t.Fatal(err)
+	}
+	_ = w2.Close()
+
+	st2, err := os.Stat(dir2)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got := st2.Mode().Perm(); got != 0o700 {
+		t.Fatalf("dir perm = %o, want 0700", got)
+	}
+}
+
+func TestDirMode_ExplicitOctal(t *testing.T) {
+	m := syscall.Umask(0)
+	defer syscall.Umask(m)
+
+	base := t.TempDir()
+	dest := filepath.Join(base, "logs3")
+	fw := &FileWriter{
+		Filename: filepath.Join(dest, "app.log"),
+		DirMode:  "0750",
+		Mode:     0o640,
+		Roll:     func() *bool { f := false; return &f }(),
+	}
+	w, err := fw.OpenWriter()
+	if err != nil {
+		t.Fatal(err)
+	}
+	_ = w.Close()
+
+	st, err := os.Stat(dest)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got := st.Mode().Perm(); got != 0o750 {
+		t.Fatalf("dir perm = %o, want 0750", got)
+	}
+}
+
+func TestDirMode_Default0700(t *testing.T) {
+	m := syscall.Umask(0)
+	defer syscall.Umask(m)
+
+	base := t.TempDir()
+	dest := filepath.Join(base, "logs4")
+	fw := &FileWriter{
+		Filename: filepath.Join(dest, "app.log"),
+		Mode:     0o640,
+		Roll:     func() *bool { f := false; return &f }(),
+	}
+	w, err := fw.OpenWriter()
+	if err != nil {
+		t.Fatal(err)
+	}
+	_ = w.Close()
+
+	st, err := os.Stat(dest)
+	if err != nil {
+		t.Fatal(err)
+	}
+	if got := st.Mode().Perm(); got != 0o700 {
+		t.Fatalf("dir perm = %o, want 0700", got)
+	}
+}
+
+func TestDirMode_UmaskInteraction(t *testing.T) {
+	_ = syscall.Umask(0o022) // typical umask; restore after
+	defer syscall.Umask(0)
+
+	base := t.TempDir()
+	dest := filepath.Join(base, "logs5")
+	fw := &FileWriter{
+		Filename: filepath.Join(dest, "app.log"),
+		DirMode:  "0755",
+		Mode:     0o644,
+		Roll:     func() *bool { f := false; return &f }(),
+	}
+	w, err := fw.OpenWriter()
+	if err != nil {
+		t.Fatal(err)
+	}
+	_ = w.Close()
+
+	st, err := os.Stat(dest)
+	if err != nil {
+		t.Fatal(err)
+	}
+	// 0755 &^ 0022 still 0755 for dirs; this just sanity-checks we didn't get stricter unexpectedly
+	if got := st.Mode().Perm(); got != 0o755 {
+		t.Fatalf("dir perm = %o, want 0755 (considering umask)", got)
+	}
+}
+
+func TestCaddyfile_DirMode_Inherit(t *testing.T) {
+	d := caddyfile.NewTestDispenser(`
+file /var/log/app.log {
+    dir_mode inherit
+    mode 0640
+}`)
+	var fw FileWriter
+	if err := fw.UnmarshalCaddyfile(d); err != nil {
+		t.Fatal(err)
+	}
+	if fw.DirMode != "inherit" {
+		t.Fatalf("got %q", fw.DirMode)
+	}
+	if fw.Mode != 0o640 {
+		t.Fatalf("mode = %o", fw.Mode)
+	}
+}
+
+func TestCaddyfile_DirMode_FromFile(t *testing.T) {
+	d := caddyfile.NewTestDispenser(`
+file /var/log/app.log {
+    dir_mode from_file
+    mode 0600
+}`)
+	var fw FileWriter
+	if err := fw.UnmarshalCaddyfile(d); err != nil {
+		t.Fatal(err)
+	}
+	if fw.DirMode != "from_file" {
+		t.Fatalf("got %q", fw.DirMode)
+	}
+	if fw.Mode != 0o600 {
+		t.Fatalf("mode = %o", fw.Mode)
+	}
+}
+
+func TestCaddyfile_DirMode_Octal(t *testing.T) {
+	d := caddyfile.NewTestDispenser(`
+file /var/log/app.log {
+    dir_mode 0755
+}`)
+	var fw FileWriter
+	if err := fw.UnmarshalCaddyfile(d); err != nil {
+		t.Fatal(err)
+	}
+	if fw.DirMode != "0755" {
+		t.Fatalf("got %q", fw.DirMode)
+	}
+}
+
+func TestCaddyfile_DirMode_Invalid(t *testing.T) {
+	d := caddyfile.NewTestDispenser(`
+file /var/log/app.log {
+    dir_mode nope
+}`)
+	var fw FileWriter
+	if err := fw.UnmarshalCaddyfile(d); err == nil {
+		t.Fatal("expected error for invalid dir_mode")
+	}
+}
@@ -53,3 +53,41 @@ func TestFileCreationMode(t *testing.T) {
 		t.Fatalf("file mode is %v, want rw for user", st.Mode().Perm())
 	}
 }
+
+func TestDirMode_Windows_CreateSucceeds(t *testing.T) {
+	dir, err := os.MkdirTemp("", "caddytest")
+	if err != nil {
+		t.Fatalf("failed to create tempdir: %v", err)
+	}
+	defer os.RemoveAll(dir)
+
+	tests := []struct {
+		name    string
+		dirMode string
+	}{
+		{"inherit", "inherit"},
+		{"from_file", "from_file"},
+		{"octal", "0755"},
+		{"default", ""},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			subdir := path.Join(dir, "logs-"+tt.name)
+			fw := &FileWriter{
+				Filename: path.Join(subdir, "test.log"),
+				DirMode:  tt.dirMode,
+				Mode:     0o600,
+			}
+			w, err := fw.OpenWriter()
+			if err != nil {
+				t.Fatalf("failed to open writer: %v", err)
+			}
+			defer w.Close()
+
+			if _, err := os.Stat(fw.Filename); err != nil {
+				t.Fatalf("expected file to exist: %v", err)
+			}
+		})
+	}
+}