diff --git a/src/extension.ts b/src/extension.ts
index 8fa37fb..d7a39f7 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -421,6 +421,15 @@ class ClaudeChatProvider {
 				data: this._draftMessage
 			});
 		}
+
+		// Restore the plan-mode toggle: its state only lives in the webview and
+		// would otherwise silently reset on every webview rebuild / VS Code restart.
+		if (this._context.workspaceState.get<boolean>('claude.planModeEnabled', false)) {
+			this._postMessage({
+				type: 'restorePlanMode',
+				data: true
+			});
+		}
 	}
 
 	private async _handleWebviewMessage(message: any) {
@@ -670,6 +679,9 @@ class ClaudeChatProvider {
 			case 'enableYoloMode':
 				this._enableYoloMode();
 				return;
+			case 'planModeChanged':
+				this._context.workspaceState.update('claude.planModeEnabled', !!message.enabled);
+				return;
 			case 'saveInputText':
 				this._saveInputText(message.text);
 				return;
diff --git a/src/script.ts b/src/script.ts
index 4c949e2..f68db00 100644
--- a/src/script.ts
+++ b/src/script.ts
@@ -954,6 +954,7 @@ const getScript = (isTelemetryEnabled: boolean, opencreditsApiUrl: string = 'htt
 
 		function togglePlanMode() {
 			planModeEnabled = !planModeEnabled;
+			vscode.postMessage({ type: 'planModeChanged', enabled: planModeEnabled });
 			const switchElement = document.getElementById('planModeSwitch');
 			if (planModeEnabled) {
 				switchElement.classList.add('active');
@@ -1009,6 +1010,7 @@ const getScript = (isTelemetryEnabled: boolean, opencreditsApiUrl: string = 'htt
 
 		function cyclePlanMode() {
 			planModeEnabled = !planModeEnabled;
+			vscode.postMessage({ type: 'planModeChanged', enabled: planModeEnabled });
 			sendStats('Plan mode toggled', { enabled: planModeEnabled });
 			var switchElement = document.getElementById('planModeSwitch');
 			var toggleBtn = document.getElementById('planToggleBtn');
@@ -3560,6 +3562,18 @@ const getScript = (isTelemetryEnabled: boolean, opencreditsApiUrl: string = 'htt
 						inputField.style.height = Math.min(inputField.scrollHeight, 200) + 'px';
 					}
 					break;
+
+				case 'restorePlanMode':
+					// Plan mode state only lives in the webview; without this restore
+					// it silently resets on every webview rebuild / VS Code restart.
+					if (message.data && !planModeEnabled) {
+						planModeEnabled = true;
+						const planSwitchEl = document.getElementById('planModeSwitch');
+						const planBtnEl = document.getElementById('planToggleBtn');
+						if (planSwitchEl) planSwitchEl.classList.add('active');
+						if (planBtnEl) planBtnEl.classList.add('active');
+					}
+					break;
 					
 				case 'output':
 					if (message.data.trim()) {