diff --git a/caddyconfig/httpcaddyfile/shorthands_test.go b/caddyconfig/httpcaddyfile/shorthands_test.go
new file mode 100644
index 000000000..ec3fd4cad
--- /dev/null
+++ b/caddyconfig/httpcaddyfile/shorthands_test.go
@@ -0,0 +1,299 @@
+package httpcaddyfile
+
+import (
+	"testing"
+
+	"github.com/caddyserver/caddy/v2/caddyconfig/caddyfile"
+)
+
+func TestShorthandReplacerSimpleReplacements(t *testing.T) {
+	sr := NewShorthandReplacer()
+
+	tests := []struct {
+		name  string
+		input string
+		want  string
+	}{
+		{
+			name:  "host",
+			input: "{host}",
+			want:  "{http.request.host}",
+		},
+		{
+			name:  "hostport",
+			input: "{hostport}",
+			want:  "{http.request.hostport}",
+		},
+		{
+			name:  "port",
+			input: "{port}",
+			want:  "{http.request.port}",
+		},
+		{
+			name:  "method",
+			input: "{method}",
+			want:  "{http.request.method}",
+		},
+		{
+			name:  "uri",
+			input: "{uri}",
+			want:  "{http.request.uri}",
+		},
+		{
+			name:  "path",
+			input: "{path}",
+			want:  "{http.request.uri.path}",
+		},
+		{
+			name:  "query",
+			input: "{query}",
+			want:  "{http.request.uri.query}",
+		},
+		{
+			name:  "scheme",
+			input: "{scheme}",
+			want:  "{http.request.scheme}",
+		},
+		{
+			name:  "remote_host",
+			input: "{remote_host}",
+			want:  "{http.request.remote.host}",
+		},
+		{
+			name:  "remote_port",
+			input: "{remote_port}",
+			want:  "{http.request.remote.port}",
+		},
+		{
+			name:  "uuid",
+			input: "{uuid}",
+			want:  "{http.request.uuid}",
+		},
+		{
+			name:  "tls_cipher",
+			input: "{tls_cipher}",
+			want:  "{http.request.tls.cipher_suite}",
+		},
+		{
+			name:  "tls_version",
+			input: "{tls_version}",
+			want:  "{http.request.tls.version}",
+		},
+		{
+			name:  "client_ip",
+			input: "{client_ip}",
+			want:  "{http.vars.client_ip}",
+		},
+		{
+			name:  "upstream_hostport",
+			input: "{upstream_hostport}",
+			want:  "{http.reverse_proxy.upstream.hostport}",
+		},
+		{
+			name:  "dir",
+			input: "{dir}",
+			want:  "{http.request.uri.path.dir}",
+		},
+		{
+			name:  "file",
+			input: "{file}",
+			want:  "{http.request.uri.path.file}",
+		},
+		{
+			name:  "orig_method",
+			input: "{orig_method}",
+			want:  "{http.request.orig_method}",
+		},
+		{
+			name:  "orig_uri",
+			input: "{orig_uri}",
+			want:  "{http.request.orig_uri}",
+		},
+		{
+			name:  "orig_path",
+			input: "{orig_path}",
+			want:  "{http.request.orig_uri.path}",
+		},
+		{
+			name:  "no matching placeholder",
+			input: "{unknown}",
+			want:  "{unknown}",
+		},
+		{
+			name:  "not a placeholder",
+			input: "plain text",
+			want:  "plain text",
+		},
+		{
+			name:  "empty string",
+			input: "",
+			want:  "",
+		},
+		{
+			name:  "multiple placeholders in one string",
+			input: "{host}:{port}",
+			want:  "{http.request.host}:{http.request.port}",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			segment := caddyfile.Segment{{Text: tt.input}}
+			sr.ApplyToSegment(&segment)
+			got := segment[0].Text
+			if got != tt.want {
+				t.Errorf("ApplyToSegment(%q) = %q, want %q", tt.input, got, tt.want)
+			}
+		})
+	}
+}
+
+func TestShorthandReplacerComplexReplacements(t *testing.T) {
+	sr := NewShorthandReplacer()
+
+	tests := []struct {
+		name  string
+		input string
+		want  string
+	}{
+		{
+			name:  "header placeholder",
+			input: "{header.X-Forwarded-For}",
+			want:  "{http.request.header.X-Forwarded-For}",
+		},
+		{
+			name:  "cookie placeholder",
+			input: "{cookie.session_id}",
+			want:  "{http.request.cookie.session_id}",
+		},
+		{
+			name:  "labels placeholder",
+			input: "{labels.0}",
+			want:  "{http.request.host.labels.0}",
+		},
+		{
+			name:  "path segment placeholder",
+			input: "{path.0}",
+			want:  "{http.request.uri.path.0}",
+		},
+		{
+			name:  "query placeholder",
+			input: "{query.page}",
+			want:  "{http.request.uri.query.page}",
+		},
+		{
+			name:  "re placeholder with dots",
+			input: "{re.name.group}",
+			want:  "{http.regexp.name.group}",
+		},
+		{
+			name:  "vars placeholder",
+			input: "{vars.my_var}",
+			want:  "{http.vars.my_var}",
+		},
+		{
+			name:  "rp placeholder",
+			input: "{rp.upstream.address}",
+			want:  "{http.reverse_proxy.upstream.address}",
+		},
+		{
+			name:  "resp placeholder",
+			input: "{resp.status_code}",
+			want:  "{http.intercept.status_code}",
+		},
+		{
+			name:  "err placeholder",
+			input: "{err.status_code}",
+			want:  "{http.error.status_code}",
+		},
+		{
+			name:  "file_match placeholder",
+			input: "{file_match.relative}",
+			want:  "{http.matchers.file.relative}",
+		},
+		{
+			name:  "header with hyphen",
+			input: "{header.Content-Type}",
+			want:  "{http.request.header.Content-Type}",
+		},
+		{
+			name:  "header with underscore",
+			input: "{header.X_Custom_Header}",
+			want:  "{http.request.header.X_Custom_Header}",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			segment := caddyfile.Segment{{Text: tt.input}}
+			sr.ApplyToSegment(&segment)
+			got := segment[0].Text
+			if got != tt.want {
+				t.Errorf("ApplyToSegment(%q) = %q, want %q", tt.input, got, tt.want)
+			}
+		})
+	}
+}
+
+func TestShorthandReplacerApplyToNilSegment(t *testing.T) {
+	sr := NewShorthandReplacer()
+	// Should not panic
+	sr.ApplyToSegment(nil)
+}
+
+func TestShorthandReplacerMultipleTokens(t *testing.T) {
+	sr := NewShorthandReplacer()
+
+	segment := caddyfile.Segment{
+		{Text: "{host}"},
+		{Text: "{path}"},
+		{Text: "{header.X-Test}"},
+		{Text: "plain"},
+	}
+
+	sr.ApplyToSegment(&segment)
+
+	expected := []string{
+		"{http.request.host}",
+		"{http.request.uri.path}",
+		"{http.request.header.X-Test}",
+		"plain",
+	}
+
+	for i, want := range expected {
+		if segment[i].Text != want {
+			t.Errorf("token %d: got %q, want %q", i, segment[i].Text, want)
+		}
+	}
+}
+
+func TestShorthandReplacerEmptySegment(t *testing.T) {
+	sr := NewShorthandReplacer()
+	segment := caddyfile.Segment{}
+	sr.ApplyToSegment(&segment) // should not panic
+}
+
+func TestShorthandReplacerEscapedPlaceholders(t *testing.T) {
+	sr := NewShorthandReplacer()
+
+	// Percent-escaped path placeholder
+	segment := caddyfile.Segment{{Text: "{%path}"}}
+	sr.ApplyToSegment(&segment)
+	if segment[0].Text != "{http.request.uri.path_escaped}" {
+		t.Errorf("got %q, want {http.request.uri.path_escaped}", segment[0].Text)
+	}
+
+	// Percent-escaped query placeholder
+	segment = caddyfile.Segment{{Text: "{%query}"}}
+	sr.ApplyToSegment(&segment)
+	if segment[0].Text != "{http.request.uri.query_escaped}" {
+		t.Errorf("got %q, want {http.request.uri.query_escaped}", segment[0].Text)
+	}
+
+	// Prefixed query
+	segment = caddyfile.Segment{{Text: "{?query}"}}
+	sr.ApplyToSegment(&segment)
+	if segment[0].Text != "{http.request.uri.prefixed_query}" {
+		t.Errorf("got %q, want {http.request.uri.prefixed_query}", segment[0].Text)
+	}
+}