diff --git a/internal/backend/watchdog_roundtriper.go b/internal/backend/watchdog_roundtriper.go
index e3e10d7fe..dc270b974 100644
--- a/internal/backend/watchdog_roundtriper.go
+++ b/internal/backend/watchdog_roundtriper.go
@@ -65,6 +65,9 @@ func (w *watchdogRoundtripper) RoundTrip(req *http.Request) (*http.Response, err
 
 	resp, err := w.rt.RoundTrip(req)
 	if err != nil {
+		if isTimeout(err) {
+			err = errRequestTimeout
+		}
 		return nil, err
 	}
 
diff --git a/internal/backend/watchdog_roundtriper_test.go b/internal/backend/watchdog_roundtriper_test.go
index 723a311cb..f7f90259c 100644
--- a/internal/backend/watchdog_roundtriper_test.go
+++ b/internal/backend/watchdog_roundtriper_test.go
@@ -135,7 +135,7 @@ func TestUploadTimeout(t *testing.T) {
 	rtest.OK(t, err)
 
 	resp, err := rt.RoundTrip(req)
-	rtest.Equals(t, context.Canceled, err)
+	rtest.Equals(t, errRequestTimeout, err)
 	// make linter happy
 	if resp != nil {
 		rtest.OK(t, resp.Body.Close())
@@ -162,7 +162,7 @@ func TestProcessingTimeout(t *testing.T) {
 	rtest.OK(t, err)
 
 	resp, err := rt.RoundTrip(req)
-	rtest.Equals(t, context.Canceled, err)
+	rtest.Equals(t, errRequestTimeout, err)
 	// make linter happy
 	if resp != nil {
 		rtest.OK(t, resp.Body.Close())