diff --git a/internal/cmd/root.go b/internal/cmd/root.go
index 1674fe0ca8b2569915543853527be79153e6b237..7ee034d4be674ad9938b370a93b284c36e7abd9e 100644
--- a/internal/cmd/root.go
+++ b/internal/cmd/root.go
@@ -382,13 +382,23 @@ func ensureServer(cmd *cobra.Command, hostURL *url.URL) error {
 	switch hostURL.Scheme {
 	case "unix", "npipe":
 		needsStart := false
-		if _, err := os.Stat(hostURL.Host); err != nil && errors.Is(err, fs.ErrNotExist) {
+		_, statErr := os.Stat(hostURL.Host)
+		switch {
+		case statErr == nil:
+			restarted, err := restartIfStale(cmd, hostURL)
+			if err != nil {
+				slog.Warn("Failed to check server version", "error", err)
+			}
+			needsStart = restarted || err != nil
+		case errors.Is(statErr, fs.ErrNotExist):
 			needsStart = true
-		} else if err == nil {
-			if err := restartIfStale(cmd, hostURL); err != nil {
-				slog.Warn("Failed to check server version, restarting", "error", err)
-				needsStart = true
+		default:
+			slog.Warn("Unexpected error stat'ing server socket, attempting cleanup",
+				"path", hostURL.Host, "error", statErr)
+			if err := os.Remove(hostURL.Host); err != nil && !errors.Is(err, fs.ErrNotExist) {
+				return fmt.Errorf("failed to remove stale server socket %q: %v", hostURL.Host, err)
 			}
+			needsStart = true
 		}
 
 		if needsStart {
@@ -517,17 +527,21 @@ func probeHealth(ctx context.Context, h *http.Client, reqURL string, hostURL *ur
 // restartIfStale checks whether the running server matches the current
 // client version. When they differ, it sends a shutdown command and
 // removes the stale socket so the caller can start a fresh server.
-func restartIfStale(cmd *cobra.Command, hostURL *url.URL) error {
+//
+// It returns restarted=true when it has shut down a stale server and the
+// caller must spawn a new one. When the server matches the client version
+// (or the check itself fails), restarted is false.
+func restartIfStale(cmd *cobra.Command, hostURL *url.URL) (restarted bool, err error) {
 	c, err := client.NewClient("", hostURL.Scheme, hostURL.Host)
 	if err != nil {
-		return err
+		return false, err
 	}
 	vi, err := c.VersionInfo(cmd.Context())
 	if err != nil {
-		return err
+		return false, err
 	}
 	if vi.Version == version.Version {
-		return nil
+		return false, nil
 	}
 	slog.Info("Server version mismatch, restarting",
 		"server", vi.Version,
@@ -541,13 +555,13 @@ func restartIfStale(cmd *cobra.Command, hostURL *url.URL) error {
 		}
 		select {
 		case <-cmd.Context().Done():
-			return cmd.Context().Err()
+			return true, cmd.Context().Err()
 		case <-time.After(100 * time.Millisecond):
 		}
 	}
 	// Force-remove if the socket is still lingering.
 	_ = os.Remove(hostURL.Host)
-	return nil
+	return true, nil
 }
 
 var safeNameRegexp = regexp.MustCompile(`[^a-zA-Z0-9._-]`)