diff --git a/packages/app/src/components/file-explorer-pane.tsx b/packages/app/src/components/file-explorer-pane.tsx
index 5d952e135..9575eb891 100644
--- a/packages/app/src/components/file-explorer-pane.tsx
+++ b/packages/app/src/components/file-explorer-pane.tsx
@@ -167,23 +167,32 @@ export function FileExplorerPane({
     if (hasInitializedRef.current) {
       return;
     }
+    // Mark initialized eagerly so concurrent effect re-runs don't double-fetch.
+    // If the root listing fails (e.g. client not yet connected), we reset the
+    // flag so the next time requestDirectoryListing is recreated (when client
+    // becomes available) this effect retries automatically.
     hasInitializedRef.current = true;
     void requestDirectoryListing(".", {
       recordHistory: false,
       setCurrentPath: false,
-    });
-    const persistedPaths =
-      usePanelStore.getState().expandedPathsByWorkspace[workspaceStateKey ?? ""];
-    if (persistedPaths) {
-      for (const path of persistedPaths) {
-        if (path !== ".") {
-          void requestDirectoryListing(path, {
-            recordHistory: false,
-            setCurrentPath: false,
-          });
+    }).then((succeeded) => {
+      if (!succeeded) {
+        hasInitializedRef.current = false;
+        return;
+      }
+      const persistedPaths =
+        usePanelStore.getState().expandedPathsByWorkspace[workspaceStateKey ?? ""];
+      if (persistedPaths) {
+        for (const path of persistedPaths) {
+          if (path !== ".") {
+            void requestDirectoryListing(path, {
+              recordHistory: false,
+              setCurrentPath: false,
+            });
+          }
         }
       }
-    }
+    });
   }, [hasWorkspaceScope, requestDirectoryListing, workspaceStateKey]);
 
   // Expand ancestor directories when a file is selected (e.g., from an inline path click)
diff --git a/packages/app/src/hooks/use-file-explorer-actions.ts b/packages/app/src/hooks/use-file-explorer-actions.ts
index 766b1f978..f23c4056e 100644
--- a/packages/app/src/hooks/use-file-explorer-actions.ts
+++ b/packages/app/src/hooks/use-file-explorer-actions.ts
@@ -82,9 +82,12 @@ export function useFileExplorerActions(params: { serverId: string } & FileExplor
   );
 
   const requestDirectoryListing = useCallback(
-    async (path: string, options?: { recordHistory?: boolean; setCurrentPath?: boolean }) => {
+    async (
+      path: string,
+      options?: { recordHistory?: boolean; setCurrentPath?: boolean },
+    ): Promise<boolean> => {
       if (!workspaceStateKey) {
-        return;
+        return false;
       }
       const normalizedPath = path && path.length > 0 ? path : ".";
       const shouldSetCurrentPath = options?.setCurrentPath ?? true;
@@ -113,7 +116,7 @@ export function useFileExplorerActions(params: { serverId: string } & FileExplor
           lastError: "Workspace is unavailable",
           pendingRequest: null,
         }));
-        return;
+        return false;
       }
 
       if (!client) {
@@ -123,7 +126,7 @@ export function useFileExplorerActions(params: { serverId: string } & FileExplor
           lastError: "Host is not connected",
           pendingRequest: null,
         }));
-        return;
+        return false;
       }
 
       try {
@@ -150,6 +153,7 @@ export function useFileExplorerActions(params: { serverId: string } & FileExplor
 
           return nextState;
         });
+        return true;
       } catch (error) {
         updateExplorerState((state) => ({
           ...state,
@@ -157,6 +161,7 @@ export function useFileExplorerActions(params: { serverId: string } & FileExplor
           lastError: error instanceof Error ? error.message : "Failed to list directory",
           pendingRequest: null,
         }));
+        return false;
       }
     },
     [client, normalizedWorkspaceRoot, updateExplorerState, workspaceStateKey],