diff --git a/admin.go b/admin.go
index 2eb9c3b04..5ceb3daeb 100644
--- a/admin.go
+++ b/admin.go
@@ -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))
diff --git a/caddy.go b/caddy.go
index 1c08de8a8..c27ae4a68 100644
--- a/caddy.go
+++ b/caddy.go
@@ -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
@@ -433,7 +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
@@ -509,7 +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)
@@ -518,7 +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 {
@@ -526,7 +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 {
@@ -746,7 +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
@@ -754,7 +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
 }
diff --git a/context.go b/context.go
index a12cdcad4..980027275 100644
--- a/context.go
+++ b/context.go
@@ -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()
diff --git a/listeners.go b/listeners.go
index 0639b16b7..84ebaaaba 100644
--- a/listeners.go
+++ b/listeners.go
@@ -512,7 +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
@@ -542,17 +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()
@@ -608,13 +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
@@ -637,7 +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)
 	}
diff --git a/modules/caddyhttp/app.go b/modules/caddyhttp/app.go
index 8058dbf33..74f1466be 100644
--- a/modules/caddyhttp/app.go
+++ b/modules/caddyhttp/app.go
@@ -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))
diff --git a/modules/caddyhttp/reverseproxy/httptransport.go b/modules/caddyhttp/reverseproxy/httptransport.go
index 8d2b99e9e..c65bd6185 100644
--- a/modules/caddyhttp/reverseproxy/httptransport.go
+++ b/modules/caddyhttp/reverseproxy/httptransport.go
@@ -448,7 +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)