diff --git a/packages/vscode/src/AgentManagerPanelProvider.ts b/packages/vscode/src/AgentManagerPanelProvider.ts
index 566f9679..e19ed9b7 100644
--- a/packages/vscode/src/AgentManagerPanelProvider.ts
+++ b/packages/vscode/src/AgentManagerPanelProvider.ts
@@ -1,4 +1,5 @@
 import * as vscode from 'vscode';
+import { scheduleCachedStateRetries } from './webviewCachedStateRetry';
 import { handleBridgeMessage, type BridgeRequest, type BridgeResponse } from './bridge';
 import { getThemeKindName } from './theme';
 import type { OpenCodeManager, ConnectionStatus } from './opencode';
@@ -23,6 +24,19 @@ export class AgentManagerPanelProvider {
   private _sseStreams = new Map<string, AbortController>();
   private readonly _webviewDevServerUrl: string | null;
 
+  /**
+   * See webviewCachedStateRetry.ts — a single postMessage can be dropped
+   * before the webview bridge is ready, leaving the loading screen stuck.
+   */
+  private _scheduleCachedStateRetries(targetPanel: vscode.WebviewPanel | undefined): void {
+    scheduleCachedStateRetries({
+      target: targetPanel ?? this._panel,
+      getCurrent: () => this._panel,
+      isConnected: () => this._cachedStatus === 'connected',
+      send: () => this._sendCachedState(),
+    });
+  }
+
   constructor(
     private readonly _context: vscode.ExtensionContext,
     private readonly _extensionUri: vscode.Uri,
@@ -64,6 +78,9 @@ export class AgentManagerPanelProvider {
 
     // Send cached connection status
     this._sendCachedState();
+    // The webview bridge may not be ready yet; keep re-sending so a dropped
+    // `connectionStatus` can never leave the webview stuck on its loading screen.
+    this._scheduleCachedStateRetries(this._panel);
 
     // Handle panel disposal
     this._panel.onDidDispose(() => {
@@ -126,6 +143,13 @@ export class AgentManagerPanelProvider {
 
     // Send to webview if it exists
     this._sendCachedState();
+
+    // When we become connected, keep re-sending at staggered delays so the
+    // webview cannot miss the transition (postMessage is dropped if the
+    // webview bridge is not ready yet).
+    if (status === 'connected') {
+      this._scheduleCachedStateRetries(this._panel);
+    }
   }
 
   public notifySettingsSynced(settings: unknown): void {
diff --git a/packages/vscode/src/ChatViewProvider.ts b/packages/vscode/src/ChatViewProvider.ts
index e6e7852c..ab547fa3 100644
--- a/packages/vscode/src/ChatViewProvider.ts
+++ b/packages/vscode/src/ChatViewProvider.ts
@@ -1,4 +1,5 @@
 import * as vscode from 'vscode';
+import { scheduleCachedStateRetries } from './webviewCachedStateRetry';
 import { handleBridgeMessage, type BridgeRequest, type BridgeResponse } from './bridge';
 import { getThemeKindName } from './theme';
 import type { OpenCodeManager, ConnectionStatus } from './opencode';
@@ -58,6 +59,19 @@ export class ChatViewProvider implements vscode.WebviewViewProvider {
   private readonly _MESSAGE_TIMEOUT = 5000; // 5 seconds
   private readonly _MAX_RETRIES = 3;
 
+  /**
+   * See webviewCachedStateRetry.ts — a single postMessage can be dropped
+   * before the webview bridge is ready, leaving the loading screen stuck.
+   */
+  private _scheduleCachedStateRetries(targetView: vscode.WebviewView | undefined): void {
+    scheduleCachedStateRetries({
+      target: targetView ?? this._view,
+      getCurrent: () => this._view,
+      isConnected: () => this._cachedStatus === 'connected',
+      send: () => this._sendCachedState(),
+    });
+  }
+
   private _createMessageId(): string {
     return `msg_${Date.now()}_${Math.random().toString(36).slice(2, 8)}`;
   }
@@ -102,6 +116,9 @@ export class ChatViewProvider implements vscode.WebviewViewProvider {
 
     // Send cached connection status and API URL (may have been set before webview was resolved)
     this._sendCachedState();
+    // The webview bridge may not be ready yet; keep re-sending so a dropped
+    // `connectionStatus` can never leave the webview stuck on its loading screen.
+    this._scheduleCachedStateRetries(webviewView);
 
     // Send current active editor file state to the new webview
     this._lastActiveEditorFilePayload = null;
@@ -185,6 +202,13 @@ export class ChatViewProvider implements vscode.WebviewViewProvider {
     
     // Send to webview if it exists
     this._sendCachedState();
+
+    // When we become connected, keep re-sending at staggered delays so the
+    // webview cannot miss the transition (postMessage is dropped if the
+    // webview bridge is not ready yet).
+    if (status === 'connected') {
+      this._scheduleCachedStateRetries(this._view);
+    }
   }
 
   public addTextToInput(text: string) {
diff --git a/packages/vscode/src/SessionEditorPanelProvider.ts b/packages/vscode/src/SessionEditorPanelProvider.ts
index 76a82b02..6150e13d 100644
--- a/packages/vscode/src/SessionEditorPanelProvider.ts
+++ b/packages/vscode/src/SessionEditorPanelProvider.ts
@@ -1,4 +1,5 @@
 import * as vscode from 'vscode';
+import { scheduleCachedStateRetries } from './webviewCachedStateRetry';
 import { handleBridgeMessage, type BridgeRequest, type BridgeResponse } from './bridge';
 import { getThemeKindName } from './theme';
 import type { OpenCodeManager, ConnectionStatus } from './opencode';
@@ -49,6 +50,19 @@ export class SessionEditorPanelProvider {
   private _lastActiveEditorFilePayload: ActiveEditorFilePayload | null = null;
   private readonly _webviewDevServerUrl: string | null;
 
+  /**
+   * See webviewCachedStateRetry.ts — a single postMessage can be dropped
+   * before the webview bridge is ready, leaving the loading screen stuck.
+   */
+  private _scheduleCachedStateRetries(panelId: string, entry: SessionPanelState): void {
+    scheduleCachedStateRetries({
+      target: entry.panel,
+      getCurrent: () => this._panels.get(panelId)?.panel,
+      isConnected: () => this._cachedStatus === 'connected',
+      send: () => this._sendCachedStateToPanel(entry),
+    });
+  }
+
   constructor(
     private readonly _context: vscode.ExtensionContext,
     private readonly _extensionUri: vscode.Uri,
@@ -116,6 +130,9 @@ export class SessionEditorPanelProvider {
 
     void this.updateTheme(vscode.window.activeColorTheme.kind);
     this._sendCachedStateToPanel(state);
+    // The webview bridge may not be ready yet; keep re-sending so a dropped
+    // `connectionStatus` can never leave the webview stuck on its loading screen.
+    this._scheduleCachedStateRetries(panelId, state);
     void this._broadcastActiveEditorFile();
 
     panel.onDidDispose(() => {
@@ -187,6 +204,15 @@ export class SessionEditorPanelProvider {
     for (const entry of this._panels.values()) {
       this._sendCachedStateToPanel(entry);
     }
+
+    // When we become connected, keep re-sending at staggered delays so the
+    // webview cannot miss the transition (postMessage is dropped if the
+    // webview bridge is not ready yet).
+    if (status === 'connected') {
+      for (const [panelId, entry] of this._panels.entries()) {
+        this._scheduleCachedStateRetries(panelId, entry);
+      }
+    }
   }
 
   public notifySettingsSynced(settings: unknown): void {
diff --git a/packages/vscode/src/webviewCachedStateRetry.ts b/packages/vscode/src/webviewCachedStateRetry.ts
new file mode 100644
index 00000000..f750c344
--- /dev/null
+++ b/packages/vscode/src/webviewCachedStateRetry.ts
@@ -0,0 +1,31 @@
+/**
+ * The webview only leaves its initial loading screen once it receives a
+ * `connectionStatus: connected` message. VS Code drops postMessage calls made
+ * before the webview's acquireVsCodeApi bridge is ready (common in
+ * code-server / slow or flaky networks), so a single send can be lost
+ * forever. Re-sending the cached state at staggered delays bounds the wait
+ * without needing a webview-side ack protocol; the payload is idempotent
+ * (connection status + window focus), so duplicate deliveries are harmless.
+ */
+const CACHED_STATE_RETRY_DELAYS_MS = [500, 1500, 3500, 7000, 12000, 20000];
+
+export function scheduleCachedStateRetries<Target>(input: {
+  /** The panel/view the retries belong to. */
+  target: Target | undefined;
+  /** Reads the provider's CURRENT panel/view, so a replaced target stops its stale retries. */
+  getCurrent: () => Target | undefined;
+  /** Retries only make sense for the connected transition. */
+  isConnected: () => boolean;
+  /** Re-sends the provider's cached state. */
+  send: () => void;
+}): void {
+  if (!input.isConnected()) return;
+  const target = input.target;
+  if (!target) return;
+  for (const delayMs of CACHED_STATE_RETRY_DELAYS_MS) {
+    setTimeout(() => {
+      if (input.getCurrent() !== target) return;
+      input.send();
+    }, delayMs);
+  }
+}