diff --git a/httpbin/handlers.go b/httpbin/handlers.go
index 1343a023b1454c83270fb66746d2039ab278af7b..5e95a9e94c0932348ef0456e0a00e51067f9f551 100644
--- a/httpbin/handlers.go
+++ b/httpbin/handlers.go
@@ -502,6 +502,7 @@ func (h *HTTPBin) Delay(w http.ResponseWriter, r *http.Request) {
 
 	select {
 	case <-r.Context().Done():
+		w.WriteHeader(499) // "Client Closed Request" https://httpstatuses.com/499
 		return
 	case <-time.After(delay):
 	}
diff --git a/httpbin/handlers_test.go b/httpbin/handlers_test.go
index e93f4f033300e736edbed642a1589df24d84692a..4371a3b0d256daaeab6920630461216a09988a25 100644
--- a/httpbin/handlers_test.go
+++ b/httpbin/handlers_test.go
@@ -5,6 +5,7 @@ import (
 	"bytes"
 	"compress/gzip"
 	"compress/zlib"
+	"context"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -1469,6 +1470,19 @@ func TestDelay(t *testing.T) {
 		}
 	})
 
+	t.Run("cancelation causes 499", func(t *testing.T) {
+		ctx, cancel := context.WithTimeout(context.Background(), 20*time.Millisecond)
+		defer cancel()
+
+		r, _ := http.NewRequestWithContext(ctx, "GET", "/delay/1s", nil)
+		w := httptest.NewRecorder()
+		handler.ServeHTTP(w, r)
+
+		if w.Code != 499 {
+			t.Errorf("expected 499 response, got %d", w.Code)
+		}
+	})
+
 	var badTests = []struct {
 		url  string
 		code int