diff --git a/changelogs/unreleased/9111-ywk253100 b/changelogs/unreleased/9111-ywk253100
new file mode 100644
index 000000000..1b5408f0b
--- /dev/null
+++ b/changelogs/unreleased/9111-ywk253100
@@ -0,0 +1 @@
+Return error if timeout when checking server version
\ No newline at end of file
diff --git a/pkg/cmd/cli/serverstatus/server_status.go b/pkg/cmd/cli/serverstatus/server_status.go
index 628c4a545..ab994e2d6 100644
--- a/pkg/cmd/cli/serverstatus/server_status.go
+++ b/pkg/cmd/cli/serverstatus/server_status.go
@@ -69,5 +69,11 @@ func (g *DefaultServerStatusGetter) GetServerStatus(kbClient kbclient.Client) (*
 
 	wait.Until(checkFunc, 250*time.Millisecond, ctx.Done())
 
-	return created, nil
+	err := ctx.Err()
+	// context.Canceled error means we have received a processed ServerStatusRequest
+	if err == context.Canceled {
+		err = nil
+	}
+
+	return created, err
 }