diff --git a/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts b/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts
index 820c2bce781..5af608b4ece 100644
--- a/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts
+++ b/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts
@@ -229,6 +229,8 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 	private _onDidChangeTaskSystemInfo: Emitter<void> = new Emitter();
 	private _willRestart: boolean = false;
 	public onDidChangeTaskSystemInfo: Event<void> = this._onDidChangeTaskSystemInfo.event;
+	private _onDidReconnectToTasks: Emitter<void> = new Emitter();
+	public onDidReconnectToTasks: Event<void> = this._onDidReconnectToTasks.event;
 
 	constructor(
 		@IConfigurationService private readonly _configurationService: IConfigurationService,
@@ -384,6 +386,7 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 		}
 		this.getWorkspaceTasks(TaskRunSource.Reconnect).then(async () => {
 			this._tasksReconnected = await this._reconnectTasks();
+			this._onDidReconnectToTasks.fire();
 		});
 	}
 
@@ -1862,6 +1865,11 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 		}
 		if (executeResult.kind === TaskExecuteKind.Active) {
 			const active = executeResult.active;
+			if (active && active.same && runSource === TaskRunSource.FolderOpen) {
+				// ignore, the task is already active, likely from being reconnected.
+				this._logService.debug('Ignoring task that is already active', executeResult.task);
+				return executeResult.promise;
+			}
 			if (active && active.same) {
 				if (this._taskSystem?.isTaskVisible(executeResult.task)) {
 					const message = nls.localize('TaskSystem.activeSame.noBackground', 'The task \'{0}\' is already active.', executeResult.task.getQualifiedLabel());
diff --git a/src/vs/workbench/contrib/tasks/browser/runAutomaticTasks.ts b/src/vs/workbench/contrib/tasks/browser/runAutomaticTasks.ts
index 0aaa08a838d..55ec14e22a0 100644
--- a/src/vs/workbench/contrib/tasks/browser/runAutomaticTasks.ts
+++ b/src/vs/workbench/contrib/tasks/browser/runAutomaticTasks.ts
@@ -28,9 +28,11 @@ export class RunAutomaticTasks extends Disposable implements IWorkbenchContribut
 		@IWorkspaceTrustManagementService private readonly _workspaceTrustManagementService: IWorkspaceTrustManagementService,
 		@ILogService private readonly _logService: ILogService) {
 		super();
-		if (this._workspaceTrustManagementService.isWorkspaceTrusted()) {
-			this._tryRunTasks();
-		}
+		this._taskService.onDidReconnectToTasks((() => {
+			if (this._workspaceTrustManagementService.isWorkspaceTrusted()) {
+				this._tryRunTasks();
+			}
+		}));
 		this._register(this._workspaceTrustManagementService.onDidChangeTrust(async trusted => {
 			if (trusted) {
 				await this._tryRunTasks();
diff --git a/src/vs/workbench/contrib/tasks/common/taskService.ts b/src/vs/workbench/contrib/tasks/common/taskService.ts
index 42236fee046..c96cba1125d 100644
--- a/src/vs/workbench/contrib/tasks/common/taskService.ts
+++ b/src/vs/workbench/contrib/tasks/common/taskService.ts
@@ -64,6 +64,7 @@ export interface IWorkspaceFolderTaskResult extends IWorkspaceTaskResult {
 export interface ITaskService {
 	readonly _serviceBrand: undefined;
 	onDidStateChange: Event<ITaskEvent>;
+	onDidReconnectToTasks: Event<void>;
 	supportsMultipleTaskExecutions: boolean;
 
 	configureAction(): Action;