diff --git a/fs.go b/fs.go
index 076602a..ef38c1c 100644
--- a/fs.go
+++ b/fs.go
@@ -247,7 +247,7 @@ func normalizeServeFilePath(ctx *RequestCtx, path string) (string, bool) {
 // Path rewriter is used in FS for translating the current request
 // to the local filesystem path relative to FS.Root.
 //
-// The returned path must not contain '/../' substrings due to security reasons,
+// The returned path must not contain '..' path segments due to security reasons,
 // since such paths may refer files outside FS.Root.
 //
 // The returned path may refer to ctx members. For example, ctx.Path().
@@ -1176,11 +1176,11 @@ func (h *fsHandler) handleRequest(ctx *RequestCtx) {
 		return
 	}
 	if h.pathRewrite != nil {
-		// There is no need to check for '/../' if path = ctx.Path(),
+		// There is no need to check rewritten paths if path = ctx.Path(),
 		// since ctx.Path must normalize and sanitize the path.
 
-		if n := bytes.Index(path, strSlashDotDotSlash); n >= 0 {
-			ctx.Logger().Printf("cannot serve path with '/../' at position %d due to security reasons: %q", n, path)
+		if hasDotDotPathSegment(path) {
+			ctx.Logger().Printf("cannot serve rewritten path with '..' path segment due to security reasons: %q", path)
 			ctx.Error("Internal Server Error", StatusInternalServerError)
 			return
 		}
@@ -1876,6 +1876,27 @@ func stripLeadingSlashes(path []byte, stripSlashes int) []byte {
 	return path
 }
 
+func hasDotDotPathSegment(path []byte) bool {
+	segmentStart := 0
+	for i := 0; i <= len(path); i++ {
+		isSeparator := i == len(path)
+		if i < len(path) {
+			isSeparator = path[i] == '/'
+			if filepath.Separator == '\\' && path[i] == '\\' {
+				isSeparator = true
+			}
+		}
+		if !isSeparator {
+			continue
+		}
+		if i-segmentStart == 2 && path[segmentStart] == '.' && path[segmentStart+1] == '.' {
+			return true
+		}
+		segmentStart = i + 1
+	}
+	return false
+}
+
 func fileExtension(path string, compressed bool, compressedFileSuffix string) string {
 	if compressed && strings.HasSuffix(path, compressedFileSuffix) {
 		path = path[:len(path)-len(compressedFileSuffix)]
diff --git a/fs_fs_test.go b/fs_fs_test.go
index 0ac58bb..9101f4b 100644
--- a/fs_fs_test.go
+++ b/fs_fs_test.go
@@ -1069,3 +1069,126 @@ func TestFSRootEnforcement(t *testing.T) {
 		})
 	}
 }
+
+func TestHasDotDotPathSegment(t *testing.T) {
+	t.Parallel()
+
+	testCases := []struct {
+		path string
+		want bool
+	}{
+		{path: "", want: false},
+		{path: ".", want: false},
+		{path: "..", want: true},
+		{path: "../secret.txt", want: true},
+		{path: "/../secret.txt", want: true},
+		{path: "nested/../info", want: true},
+		{path: "nested/..", want: true},
+		{path: "nested/..hidden/info", want: false},
+		{path: "nested..", want: false},
+		{path: "/index.html", want: false},
+	}
+
+	if filepath.Separator == '\\' {
+		testCases = append(testCases,
+			struct {
+				path string
+				want bool
+			}{path: `..\secret.txt`, want: true},
+			struct {
+				path string
+				want bool
+			}{path: `nested\..\info`, want: true},
+		)
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.path, func(t *testing.T) {
+			t.Parallel()
+
+			if got := hasDotDotPathSegment([]byte(tc.path)); got != tc.want {
+				t.Fatalf("unexpected result for %q: got %v want %v", tc.path, got, tc.want)
+			}
+		})
+	}
+}
+
+func TestFSPathRewriteRejectsDotDotSegments(t *testing.T) {
+	t.Parallel()
+
+	tmpDir := t.TempDir()
+	publicDir := filepath.Join(tmpDir, "public")
+	if err := os.MkdirAll(publicDir, 0o755); err != nil {
+		t.Fatalf("cannot create public dir: %v", err)
+	}
+	if err := os.WriteFile(filepath.Join(publicDir, "index.html"), []byte("<h1>Public</h1>"), 0o644); err != nil {
+		t.Fatalf("cannot create public index: %v", err)
+	}
+	secretPath := filepath.Join(tmpDir, "secret.txt")
+	if err := os.WriteFile(secretPath, []byte("TOP_SECRET"), 0o644); err != nil {
+		t.Fatalf("cannot create secret file: %v", err)
+	}
+
+	type testCase struct {
+		name        string
+		pathRewrite PathRewriteFunc
+		requestURI  string
+	}
+
+	testCases := []testCase{
+		{
+			name:        "prefix-stripper-leading-dotdot",
+			pathRewrite: NewPathPrefixStripper(len("/static/")),
+			requestURI:  "http://localhost/aaaaaaa../secret.txt",
+		},
+		{
+			name: "custom-leading-dotdot",
+			pathRewrite: func(ctx *RequestCtx) []byte {
+				return []byte("../secret.txt")
+			},
+			requestURI: "http://localhost/ignored",
+		},
+		{
+			name: "custom-trailing-dotdot",
+			pathRewrite: func(ctx *RequestCtx) []byte {
+				return []byte("nested/..")
+			},
+			requestURI: "http://localhost/ignored",
+		},
+		{
+			name: "custom-exact-dotdot",
+			pathRewrite: func(ctx *RequestCtx) []byte {
+				return []byte("..")
+			},
+			requestURI: "http://localhost/ignored",
+		},
+	}
+
+	for _, tc := range testCases {
+		t.Run(tc.name, func(t *testing.T) {
+			stop := make(chan struct{})
+			defer close(stop)
+
+			fs := &FS{
+				Root:           publicDir,
+				AllowEmptyRoot: true,
+				CleanStop:      stop,
+				PathRewrite:    tc.pathRewrite,
+			}
+			h := fs.NewRequestHandler()
+
+			var ctx RequestCtx
+			ctx.Init(&Request{}, nil, TestLogger{t: t})
+			ctx.Request.SetRequestURI(tc.requestURI)
+
+			h(&ctx)
+
+			if ctx.Response.StatusCode() != StatusInternalServerError {
+				t.Fatalf("unexpected status code for %s: %d. Expecting %d", tc.name, ctx.Response.StatusCode(), StatusInternalServerError)
+			}
+			if bytes.Contains(ctx.Response.Body(), []byte("TOP_SECRET")) {
+				t.Fatalf("unexpected secret disclosure for %s", tc.name)
+			}
+		})
+	}
+}