diff --git a/cmd/tailscale/cli/web.go b/cmd/tailscale/cli/web.go
index ecfb5c481..38fb737e5 100644
--- a/cmd/tailscale/cli/web.go
+++ b/cmd/tailscale/cli/web.go
@@ -321,6 +321,10 @@ func tailscaleUpForceReauth(ctx context.Context) (authURL string, retErr error)
 	})
 	bc.StartLoginInteractive()
 
+	<-pumpCtx.Done() // wait for authURL or complete failure
+	if authURL == "" && retErr == nil {
+		retErr = pumpCtx.Err()
+	}
 	if authURL == "" && retErr == nil {
 		return "", fmt.Errorf("login failed with no backend error message")
 	}