diff --git a/doc/godebug.md b/doc/godebug.md
index 86e02e820cd85518edb74d85ed4366921101f0cd..b3a43664c42cd4ab6fcd4cc59abd15e25da469e2 100644
--- a/doc/godebug.md
+++ b/doc/godebug.md
@@ -200,6 +200,15 @@ This behavior is controlled by the `x509keypairleaf` setting. For Go 1.23, it
 defaults to `x509keypairleaf=1`. Previous versions default to
 `x509keypairleaf=0`.
 
+Go 1.23 changed
+[`net/http.ServeContent`](/pkg/net/http#ServeContent),
+[`net/http.ServeFile`](/pkg/net/http#ServeFile), and
+[`net/http.ServeFS`](/pkg/net/http#ServeFS) to
+remove Cache-Control, Content-Encoding, Etag, and Last-Modified headers
+when serving an error. This behavior is controlled by
+the [`httpservecontentkeepheaders` setting](/pkg/net/http#ServeContent).
+Using `httpservecontentkeepheaders=1` restores the pre-Go 1.23 behavior.
+
 ### Go 1.22
 
 Go 1.22 adds a configurable limit to control the maximum acceptable RSA key size
diff --git a/doc/next/6-stdlib/99-minor/net/http/66343.md b/doc/next/6-stdlib/99-minor/net/http/66343.md
index 128ce68d45ebeb1e466e219ae5f5e84e04ec1d72..b39e8624e7def10396ab034cbff3c620eca5b1ef 100644
--- a/doc/next/6-stdlib/99-minor/net/http/66343.md
+++ b/doc/next/6-stdlib/99-minor/net/http/66343.md
@@ -1 +1,16 @@
-[Error] now removes misleading response headers.
+[ServeContent], [ServeFile], and [ServeFileFS] now remove
+the `Cache-Control`, `Content-Encoding`, `Etag`, and `Last-Modified`
+headers when serving an error. These headers usually apply to the
+non-error content, but not to the text of errors.
+
+Middleware which wraps a [ResponseWriter] and applies on-the-fly
+encoding, such as `Content-Encoding: gzip`, will not function after
+this change.  The previous behavior of [ServeContent], [ServeFile],
+and [ServeFileFS] may be restored by setting
+`GODEBUG=httpservecontentkeepheaders=1`.
+
+Note that middleware which changes the size of the served content
+(such as by compressing it) already does not function properly when
+[ServeContent] handles a Range request. On-the-fly compression
+should use the `Transfer-Encoding` header instead of `Content-Encoding`.
+
diff --git a/src/internal/godebugs/table.go b/src/internal/godebugs/table.go
index eb512559168c32e76eeb2f3954782cc3a548e0ec..f4262b6695d03237278d1ab260753a4678c4f007 100644
--- a/src/internal/godebugs/table.go
+++ b/src/internal/godebugs/table.go
@@ -36,6 +36,7 @@ var All = []Info{
 	{Name: "http2server", Package: "net/http"},
 	{Name: "httplaxcontentlength", Package: "net/http", Changed: 22, Old: "1"},
 	{Name: "httpmuxgo121", Package: "net/http", Changed: 22, Old: "1"},
+	{Name: "httpservecontentkeepheaders", Package: "net/http", Changed: 23, Old: "0"},
 	{Name: "installgoroot", Package: "go/build"},
 	{Name: "jstmpllitinterp", Package: "html/template", Opaque: true}, // bug #66217: remove Opaque
 	//{Name: "multipartfiles", Package: "mime/multipart"},
diff --git a/src/net/http/fs.go b/src/net/http/fs.go
index c213d8a328564c3dc13284b73c9367c306af0809..70653550f027f61bcbdfe9738b05dcc80ea0b485 100644
--- a/src/net/http/fs.go
+++ b/src/net/http/fs.go
@@ -9,6 +9,7 @@ package http
 import (
 	"errors"
 	"fmt"
+	"internal/godebug"
 	"io"
 	"io/fs"
 	"mime"
@@ -171,15 +172,37 @@ func dirList(w ResponseWriter, r *Request, f File) {
 	fmt.Fprintf(w, "</pre>\n")
 }
 
+// GODEBUG=httpservecontentkeepheaders=1 restores the pre-1.23 behavior of not deleting
+// Cache-Control, Content-Encoding, Etag, or Last-Modified headers on ServeContent errors.
+var httpservecontentkeepheaders = godebug.New("httpservecontentkeepheaders")
+
 // serveError serves an error from ServeFile, ServeFileFS, and ServeContent.
 // Because those can all be configured by the caller by setting headers like
 // Etag, Last-Modified, and Cache-Control to send on a successful response,
 // the error path needs to clear them, since they may not be meant for errors.
 func serveError(w ResponseWriter, text string, code int) {
 	h := w.Header()
-	h.Del("Etag")
-	h.Del("Last-Modified")
-	h.Del("Cache-Control")
+
+	nonDefault := false
+	for _, k := range []string{
+		"Cache-Control",
+		"Content-Encoding",
+		"Etag",
+		"Last-Modified",
+	} {
+		if !h.has(k) {
+			continue
+		}
+		if httpservecontentkeepheaders.Value() == "1" {
+			nonDefault = true
+		} else {
+			h.Del(k)
+		}
+	}
+	if nonDefault {
+		httpservecontentkeepheaders.IncNonDefault()
+	}
+
 	Error(w, text, code)
 }
 
@@ -203,11 +226,17 @@ func serveError(w ResponseWriter, text string, code int) {
 //
 // The content's Seek method must work: ServeContent uses
 // a seek to the end of the content to determine its size.
+// Note that [*os.File] implements the [io.ReadSeeker] interface.
 //
 // If the caller has set w's ETag header formatted per RFC 7232, section 2.3,
 // ServeContent uses it to handle requests using If-Match, If-None-Match, or If-Range.
 //
-// Note that [*os.File] implements the [io.ReadSeeker] interface.
+// If an error occurs when serving the request (for example, when
+// handling an invalid range request), ServeContent responds with an
+// error message. By default, ServeContent strips the Cache-Control,
+// Content-Encoding, ETag, and Last-Modified headers from error responses.
+// The GODEBUG setting httpservecontentkeepheaders=1 causes ServeContent
+// to preserve these headers.
 func ServeContent(w ResponseWriter, req *Request, name string, modtime time.Time, content io.ReadSeeker) {
 	sizeFunc := func() (int64, error) {
 		size, err := content.Seek(0, io.SeekEnd)
diff --git a/src/net/http/fs_test.go b/src/net/http/fs_test.go
index 2c3426f735271f63e65b22b75b1ed2346d4f026e..2ffffbf0b33c9705fdd22f2199f7ee71f6b4c9d3 100644
--- a/src/net/http/fs_test.go
+++ b/src/net/http/fs_test.go
@@ -1223,8 +1223,20 @@ type issue12991File struct{ File }
 func (issue12991File) Stat() (fs.FileInfo, error) { return nil, fs.ErrPermission }
 func (issue12991File) Close() error               { return nil }
 
-func TestFileServerErrorMessages(t *testing.T) { run(t, testFileServerErrorMessages) }
-func testFileServerErrorMessages(t *testing.T, mode testMode) {
+func TestFileServerErrorMessages(t *testing.T) {
+	run(t, func(t *testing.T, mode testMode) {
+		t.Run("keepheaders=0", func(t *testing.T) {
+			testFileServerErrorMessages(t, mode, false)
+		})
+		t.Run("keepheaders=1", func(t *testing.T) {
+			testFileServerErrorMessages(t, mode, true)
+		})
+	}, testNotParallel)
+}
+func testFileServerErrorMessages(t *testing.T, mode testMode, keepHeaders bool) {
+	if keepHeaders {
+		t.Setenv("GODEBUG", "httpservecontentkeepheaders=1")
+	}
 	fs := fakeFS{
 		"/500": &fakeFileInfo{
 			err: errors.New("random error"),
@@ -1254,8 +1266,12 @@ func testFileServerErrorMessages(t *testing.T, mode testMode) {
 			t.Errorf("GET /%d: StatusCode = %d; want %d", code, res.StatusCode, code)
 		}
 		for _, hdr := range []string{"Etag", "Last-Modified", "Cache-Control"} {
-			if v, ok := res.Header[hdr]; ok {
-				t.Errorf("GET /%d: Header[%q] = %q, want not present", code, hdr, v)
+			if v, got := res.Header[hdr]; got != keepHeaders {
+				want := "not present"
+				if keepHeaders {
+					want = "present"
+				}
+				t.Errorf("GET /%d: Header[%q] = %q, want %v", code, hdr, v, want)
 			}
 		}
 	}
@@ -1710,6 +1726,17 @@ func testFileServerDirWithRootFile(t *testing.T, mode testMode) {
 }
 
 func TestServeContentHeadersWithError(t *testing.T) {
+	t.Run("keepheaders=0", func(t *testing.T) {
+		testServeContentHeadersWithError(t, false)
+	})
+	t.Run("keepheaders=1", func(t *testing.T) {
+		testServeContentHeadersWithError(t, true)
+	})
+}
+func testServeContentHeadersWithError(t *testing.T, keepHeaders bool) {
+	if keepHeaders {
+		t.Setenv("GODEBUG", "httpservecontentkeepheaders=1")
+	}
 	contents := []byte("content")
 	ts := newClientServerTest(t, http1Mode, HandlerFunc(func(w ResponseWriter, r *Request) {
 		w.Header().Set("Content-Type", "application/octet-stream")
@@ -1738,6 +1765,12 @@ func TestServeContentHeadersWithError(t *testing.T) {
 	out, _ := io.ReadAll(res.Body)
 	res.Body.Close()
 
+	ifKept := func(s string) string {
+		if keepHeaders {
+			return s
+		}
+		return ""
+	}
 	if g, e := res.StatusCode, 416; g != e {
 		t.Errorf("got status = %d; want %d", g, e)
 	}
@@ -1750,16 +1783,16 @@ func TestServeContentHeadersWithError(t *testing.T) {
 	if g, e := res.Header.Get("Content-Length"), strconv.Itoa(len(out)); g != e {
 		t.Errorf("got content-length = %q, want %q", g, e)
 	}
-	if g, e := res.Header.Get("Content-Encoding"), ""; g != e {
+	if g, e := res.Header.Get("Content-Encoding"), ifKept("gzip"); g != e {
 		t.Errorf("got content-encoding = %q, want %q", g, e)
 	}
-	if g, e := res.Header.Get("Etag"), ""; g != e {
+	if g, e := res.Header.Get("Etag"), ifKept(`"abcdefgh"`); g != e {
 		t.Errorf("got etag = %q, want %q", g, e)
 	}
-	if g, e := res.Header.Get("Last-Modified"), ""; g != e {
+	if g, e := res.Header.Get("Last-Modified"), ifKept("Wed, 21 Oct 2015 07:28:00 GMT"); g != e {
 		t.Errorf("got last-modified = %q, want %q", g, e)
 	}
-	if g, e := res.Header.Get("Cache-Control"), ""; g != e {
+	if g, e := res.Header.Get("Cache-Control"), ifKept("immutable"); g != e {
 		t.Errorf("got cache-control = %q, want %q", g, e)
 	}
 	if g, e := res.Header.Get("Content-Range"), "bytes */7"; g != e {
diff --git a/src/net/http/serve_test.go b/src/net/http/serve_test.go
index 06bf5089d8fe63ae48627f429d8a827cf72a6789..3ec10c2f14da56d0ac2c3cfb96db944919658373 100644
--- a/src/net/http/serve_test.go
+++ b/src/net/http/serve_test.go
@@ -7166,13 +7166,12 @@ func testErrorContentLength(t *testing.T, mode testMode) {
 func TestError(t *testing.T) {
 	w := httptest.NewRecorder()
 	w.Header().Set("Content-Length", "1")
-	w.Header().Set("Content-Encoding", "ascii")
 	w.Header().Set("X-Content-Type-Options", "scratch and sniff")
 	w.Header().Set("Other", "foo")
 	Error(w, "oops", 432)
 
 	h := w.Header()
-	for _, hdr := range []string{"Content-Length", "Content-Encoding"} {
+	for _, hdr := range []string{"Content-Length"} {
 		if v, ok := h[hdr]; ok {
 			t.Errorf("%s: %q, want not present", hdr, v)
 		}
diff --git a/src/net/http/server.go b/src/net/http/server.go
index 190f56501379b0eb43af91a2ff7ba8a5b6d3ad8c..a5e98f1d957dcba585d501cf3dcafc833d2e5ee3 100644
--- a/src/net/http/server.go
+++ b/src/net/http/server.go
@@ -2226,17 +2226,22 @@ func (f HandlerFunc) ServeHTTP(w ResponseWriter, r *Request) {
 // writes are done to w.
 // The error message should be plain text.
 //
-// Error deletes the Content-Length and Content-Encoding headers,
+// Error deletes the Content-Length header,
 // sets Content-Type to “text/plain; charset=utf-8”,
 // and sets X-Content-Type-Options to “nosniff”.
 // This configures the header properly for the error message,
 // in case the caller had set it up expecting a successful output.
 func Error(w ResponseWriter, error string, code int) {
 	h := w.Header()
-	// We delete headers which might be valid for some other content,
-	// but not anymore for the error content.
+
+	// Delete the Content-Length header, which might be for some other content.
+	// Assuming the error string fits in the writer's buffer, we'll figure
+	// out the correct Content-Length for it later.
+	//
+	// We don't delete Content-Encoding, because some middleware sets
+	// Content-Encoding: gzip and wraps the ResponseWriter to compress on-the-fly.
+	// See https://go.dev/issue/66343.
 	h.Del("Content-Length")
-	h.Del("Content-Encoding")
 
 	// There might be content type already set, but we reset it to
 	// text/plain for the error message.
diff --git a/src/runtime/metrics/doc.go b/src/runtime/metrics/doc.go
index c1d0ca90727e84d7014c46d7d572bb4364a7a05d..b8be9f8272ba76e9e2bbbc0b37d3e83c40b51312 100644
--- a/src/runtime/metrics/doc.go
+++ b/src/runtime/metrics/doc.go
@@ -267,6 +267,11 @@ Below is the full list of supported metrics, ordered lexicographically.
 		The number of non-default behaviors executed by the net/http
 		package due to a non-default GODEBUG=httpmuxgo121=... setting.
 
+	/godebug/non-default-behavior/httpservecontentkeepheaders:events
+		The number of non-default behaviors executed
+		by the net/http package due to a non-default
+		GODEBUG=httpservecontentkeepheaders=... setting.
+
 	/godebug/non-default-behavior/installgoroot:events
 		The number of non-default behaviors executed by the go/build
 		package due to a non-default GODEBUG=installgoroot=... setting.