diff --git a/internal/frontend/frontend.go b/internal/frontend/frontend.go
index 12d1297..1a678fe 100644
--- a/internal/frontend/frontend.go
+++ b/internal/frontend/frontend.go
@@ -48,7 +48,8 @@ func Assets() fs.FS {
 // NewHandler returns a handler that serves files from fsys. A GET or HEAD for a
 // path that is not a file in fsys is answered with index.html so client-side
 // routes load the app. Paths equal to or under a reserved prefix (for example
-// "/api") are never answered with index.html; they are passed to notFound.
+// "/api") are never answered with index.html, whether before or after the path
+// is cleaned; they are passed to notFound.
 // fsys must contain index.html.
 func NewHandler(fsys fs.FS, logger *slog.Logger, notFound http.Handler, reserved ...string) (http.Handler, error) {
 	if _, err := fs.Stat(fsys, indexFile); err != nil {
@@ -66,7 +67,9 @@ type handler struct {
 
 func (h *handler) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 	urlPath := path.Clean("/" + r.URL.Path)
-	if h.isReserved(urlPath) {
+	// Check the uncleaned path too, so dot segments cannot escape a reserved
+	// prefix into the fallback ("/auth/../quests/42" cleans to "/quests/42").
+	if h.isReserved(r.URL.Path) || h.isReserved(urlPath) {
 		h.notFound.ServeHTTP(w, r)
 		return
 	}
diff --git a/internal/frontend/frontend_test.go b/internal/frontend/frontend_test.go
index 2564b2d..b6aa8c0 100644
--- a/internal/frontend/frontend_test.go
+++ b/internal/frontend/frontend_test.go
@@ -12,6 +12,7 @@ import (
 const (
 	indexBody    = "<!doctype html><title>fixture index</title>"
 	assetBody    = "console.log('fixture asset')"
+	robotsBody   = "User-agent: *"
 	swBody       = "self.addEventListener('fetch', () => {})"
 	manifestBody = `{"name":"MealQuest"}`
 	notFoundBody = "reserved not found"
@@ -23,6 +24,7 @@ func fixture() fstest.MapFS {
 		"sw.js":                  {Data: []byte(swBody)},
 		"manifest.webmanifest":   {Data: []byte(manifestBody)},
 		"assets/index-AbC123.js": {Data: []byte(assetBody)},
+		"robots.txt":             {Data: []byte(robotsBody)},
 	}
 }
 
@@ -50,6 +52,7 @@ func TestServe(t *testing.T) {
 		wantCache string
 	}{
 		{"hashed asset", http.MethodGet, "/assets/index-AbC123.js", assetBody, cacheImmutable},
+		{"unhashed asset", http.MethodGet, "/robots.txt", robotsBody, cacheImmutable},
 		{"root", http.MethodGet, "/", indexBody, cacheNoCache},
 		{"index.html", http.MethodGet, "/index.html", indexBody, cacheNoCache},
 		{"service worker", http.MethodGet, "/sw.js", swBody, cacheNoCache},
@@ -97,7 +100,7 @@ func TestReservedPrefixesNotServed(t *testing.T) {
 	t.Parallel()
 
 	h := newTestHandler(t)
-	for _, path := range []string{"/api", "/api/unknown", "/auth/login", "/media/x.jpg", "/health", "/health/deep", "/x/../api/unknown"} {
+	for _, path := range []string{"/api", "/api/unknown", "/auth/login", "/media/x.jpg", "/health", "/health/deep", "/x/../api/unknown", "/auth/../quests/42", "/api%2F..%2Fquests/42"} {
 		t.Run(path, func(t *testing.T) {
 			t.Parallel()
 
diff --git a/internal/server/server_test.go b/internal/server/server_test.go
index 400ecc0..f1adc7e 100644
--- a/internal/server/server_test.go
+++ b/internal/server/server_test.go
@@ -102,6 +102,8 @@ func TestReservedPathsNotFound(t *testing.T) {
 		{http.MethodGet, "/auth/callback"},
 		{http.MethodGet, "/media/photo.jpg"},
 		{http.MethodGet, "/health/deep"},
+		{http.MethodGet, "/auth/../quests/42"},
+		{http.MethodGet, "/api%2F..%2Fquests/42"},
 	}
 	for _, tt := range tests {
 		t.Run(tt.method+" "+tt.path, func(t *testing.T) {
@@ -135,6 +137,7 @@ func TestFrontend(t *testing.T) {
 		{"/", fixtureIndex, "no-cache"},
 		{"/assets/index-AbC123.js", fixtureAsset, "public, max-age=31536000, immutable"},
 		{"/quests/42", fixtureIndex, "no-cache"},
+		{"/quests/42/edit", fixtureIndex, "no-cache"},
 	}
 	for _, tt := range tests {
 		t.Run(tt.path, func(t *testing.T) {