fix: Handle workspace restart when DWO restarts the pod before the restart command reaches the browser

code/extensions/che-remote/src/extension.ts

@@ -242,9 +242,22 @@ async function updateDevfile(cheApi: any): Promise<boolean> {
     return false;
   }
 
+  try {
+    await vscode.commands.executeCommand('che-remote.command.prepareForRestart');
+  } catch (error) {
+    // Best-effort: if the signal doesn't reach the browser, the restart
+    // flow falls back to the normal disconnection handling.
+  }
+
   try {
     await devfileService.updateDevfile(devfileContext.devWorkspace.spec?.template);
   } catch (error) {
+    try {
+      await vscode.commands.executeCommand('che-remote.command.cancelRestart');
+    } catch (_) {
+      // best-effort cleanup
+    }
+
     if (error.body && error.body.message) {
       const action = await vscode.window.showErrorMessage('Failed to update Devfile.', {
         modal: true,

code/src/vs/workbench/contrib/remote/browser/che/devWorkspaceAssistant.ts

@@ -47,7 +47,13 @@ export class DevWorkspaceAssistant {
 	private static readonly POLL_INTERVAL_MS = 2000;
 	private static readonly STOP_TIMEOUT_MS = 10000;
 
-	private _isStopping = false;
+	/**
+	 * Tracks the intentional workspace lifecycle action in progress:
+	 * - 'idle': no action, disconnection handler shows normal dialogs
+	 * - 'restartPending': devfile update is about to happen; if extension host dies, redirect to dashboard
+	 * - 'stopping': doRestart/stopWorkspace is running on browser side, handler should not interfere
+	 */
+	private _pendingAction: 'idle' | 'restartPending' | 'stopping' = 'idle';
 	private dashboardUrl: string | undefined;
 	private getDevWorkspaceUrl: string | undefined;
 	private startingDevWorkspaceUrl: string | undefined;
@@ -62,6 +68,12 @@ export class DevWorkspaceAssistant {
 		CommandsRegistry.registerCommand('che-remote.command.stopWorkspaceAndRedirectToDashboard', () => {
 			this.stopWorkspaceAndRedirectToDashboard();
 		});
+		CommandsRegistry.registerCommand('che-remote.command.prepareForRestart', () => {
+			this._pendingAction = 'restartPending';
+		});
+		CommandsRegistry.registerCommand('che-remote.command.cancelRestart', () => {
+			this._pendingAction = 'idle';
+		});
 	}
 
 	async getDevWorkspace(): Promise<DevWorkspaceLike> {
@@ -193,29 +205,29 @@ export class DevWorkspaceAssistant {
 		);
 	}
 
-	get isStopping(): boolean {
-		return this._isStopping;
+	get pendingAction(): 'idle' | 'restartPending' | 'stopping' {
+		return this._pendingAction;
 	}
 
 	private async doRestart(): Promise<void> {
-		this._isStopping = true;
+		this._pendingAction = 'stopping';
 		try {
 			await this.stopWorkspaceViaDashboardApi();
 			await this.waitForStopped();
 			this.startWorkspace();
 		} catch (e) {
-			this._isStopping = false;
+			this._pendingAction = 'idle';
 			throw e;
 		}
 	}
 
 	async stopWorkspaceAndRedirectToDashboard(): Promise<void> {
-		this._isStopping = true;
+		this._pendingAction = 'stopping';
 		try {
 			await this.stopWorkspaceViaDashboardApi();
 			this.goToDashboard();
 		} catch (e) {
-			this._isStopping = false;
+			this._pendingAction = 'idle';
 			throw e;
 		}
 	}

code/src/vs/workbench/contrib/remote/browser/che/remote.ts

@@ -95,7 +95,12 @@ export class CheDisconnectionHandler {
 			return;
 		}
 
-		if (this.devWorkspaceAssistant.isStopping) {
+		const pendingAction = this.devWorkspaceAssistant.pendingAction;
+		if (pendingAction === 'restartPending') {
+			this.devWorkspaceAssistant.startWorkspace();
+			return;
+		}
+		if (pendingAction === 'stopping') {
 			return;
 		}