diff --git a/caddyhttp/proxy/proxy.go b/caddyhttp/proxy/proxy.go
index 5b386020e..aeff1b8f3 100644
--- a/caddyhttp/proxy/proxy.go
+++ b/caddyhttp/proxy/proxy.go
@@ -262,6 +262,10 @@ func (p Proxy) ServeHTTP(w http.ResponseWriter, r *http.Request) (int, error) {
 			return http.StatusRequestEntityTooLarge, backendErr
 		}
 
+		if backendErr == context.Canceled {
+			return CustomStatusContextCancelled, backendErr
+		}
+
 		// failover; remember this failure for some time if
 		// request failure counting is enabled
 		timeout := host.FailTimeout
@@ -397,3 +401,5 @@ func mutateHeadersByRules(headers, rules http.Header, repl httpserver.Replacer)
 		}
 	}
 }
+
+const CustomStatusContextCancelled = 499
diff --git a/caddyhttp/proxy/proxy_test.go b/caddyhttp/proxy/proxy_test.go
index caf2e6c99..1342b2bea 100644
--- a/caddyhttp/proxy/proxy_test.go
+++ b/caddyhttp/proxy/proxy_test.go
@@ -1369,7 +1369,7 @@ func TestCancelRequest(t *testing.T) {
 
 	rec := httptest.NewRecorder()
 	status, err := p.ServeHTTP(rec, req)
-	expectedStatus, expectErr := http.StatusBadGateway, context.Canceled
+	expectedStatus, expectErr := CustomStatusContextCancelled, context.Canceled
 	if status != expectedStatus || err != expectErr {
 		t.Errorf("expect proxy handle return status[%d] with error[%v], but got status[%d] with error[%v]",
 			expectedStatus, expectErr, status, err)