diff --git a/cmd/tailscale/cli/ping.go b/cmd/tailscale/cli/ping.go
index 5eb968734..5fe338da5 100644
--- a/cmd/tailscale/cli/ping.go
+++ b/cmd/tailscale/cli/ping.go
@@ -121,6 +121,12 @@ func runPing(ctx context.Context, args []string) error {
 		if err != nil {
 			if errors.Is(err, context.DeadlineExceeded) {
 				printf("ping %q timed out\n", ip)
+				if n == pingArgs.num {
+					if !anyPong {
+						return errors.New("no reply")
+					}
+					return nil
+				}
 				continue
 			}
 			return err