diff --git a/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts b/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts
index 12fc22bd477..5dc0f99ea57 100644
--- a/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts
+++ b/src/vs/workbench/contrib/tasks/browser/abstractTaskService.ts
@@ -47,7 +47,7 @@ import { ITextFileService } from 'vs/workbench/services/textfile/common/textfile
 import { ITerminalGroupService, ITerminalService } from 'vs/workbench/contrib/terminal/browser/terminal';
 import { ITerminalProfileResolverService } from 'vs/workbench/contrib/terminal/common/terminal';
 
-import { ConfiguringTask, ContributedTask, CustomTask, ExecutionEngine, InMemoryTask, ITaskEvent, ITaskIdentifier, ITaskSet, JsonSchemaVersion, KeyedTaskIdentifier, RuntimeType, Task, TaskDefinition, TaskEventKind, TaskGroup, TaskRunSource, TaskSettingId, TaskSorter, TaskSourceKind, TasksSchemaProperties, TASK_RUNNING_STATE, USER_TASKS_GROUP_KEY } from 'vs/workbench/contrib/tasks/common/tasks';
+import { ConfiguringTask, ContributedTask, CustomTask, ExecutionEngine, InMemoryTask, ITaskEvent, ITaskIdentifier, ITaskSet, JsonSchemaVersion, KeyedTaskIdentifier, RuntimeType, Task, TASK_RUNNING_STATE, TaskDefinition, TaskEventKind, TaskGroup, TaskRunSource, TaskSettingId, TaskSorter, TaskSourceKind, TasksSchemaProperties, USER_TASKS_GROUP_KEY } from 'vs/workbench/contrib/tasks/common/tasks';
 import { CustomExecutionSupportedContext, ICustomizationProperties, IProblemMatcherRunOptions, ITaskFilter, ITaskProvider, ITaskService, IWorkspaceFolderTaskResult, ProcessExecutionSupportedContext, ServerlessWebContext, ShellExecutionSupportedContext, TaskCommandsRegistered, TaskExecutionSupportedContext } from 'vs/workbench/contrib/tasks/common/taskService';
 import { ITaskExecuteResult, ITaskResolver, ITaskSummary, ITaskSystem, ITaskSystemInfo, ITaskTerminateResponse, TaskError, TaskErrors, TaskExecuteKind } from 'vs/workbench/contrib/tasks/common/taskSystem';
 import { getTemplates as getTaskTemplates } from 'vs/workbench/contrib/tasks/common/taskTemplates';
@@ -60,15 +60,18 @@ import { IQuickInputService, IQuickPick, IQuickPickItem, IQuickPickSeparator, Qu
 import { IContextKey, IContextKeyService } from 'vs/platform/contextkey/common/contextkey';
 import { TaskDefinitionRegistry } from 'vs/workbench/contrib/tasks/common/taskDefinitionRegistry';
 
+import { raceTimeout } from 'vs/base/common/async';
 import { CancellationToken, CancellationTokenSource } from 'vs/base/common/cancellation';
 import { once } from 'vs/base/common/functional';
 import { toFormattedString } from 'vs/base/common/jsonFormatter';
 import { Schemas } from 'vs/base/common/network';
+import { ThemeIcon } from 'vs/base/common/themables';
 import { IResolvedTextEditorModel, ITextModelService } from 'vs/editor/common/services/resolverService';
 import { TextEditorSelectionRevealType } from 'vs/platform/editor/common/editor';
+import { IInstantiationService } from 'vs/platform/instantiation/common/instantiation';
 import { ILogService } from 'vs/platform/log/common/log';
+import { TerminalExitReason } from 'vs/platform/terminal/common/terminal';
 import { IThemeService } from 'vs/platform/theme/common/themeService';
-import { ThemeIcon } from 'vs/base/common/themables';
 import { IWorkspaceTrustManagementService, IWorkspaceTrustRequestService } from 'vs/platform/workspace/common/workspaceTrust';
 import { VirtualWorkspaceContext } from 'vs/workbench/common/contextkeys';
 import { EditorResourceAccessor, SaveReason } from 'vs/workbench/common/editor';
@@ -79,10 +82,7 @@ import { ILifecycleService, ShutdownReason, StartupKind } from 'vs/workbench/ser
 import { IPaneCompositePartService } from 'vs/workbench/services/panecomposite/browser/panecomposite';
 import { IPathService } from 'vs/workbench/services/path/common/pathService';
 import { IPreferencesService } from 'vs/workbench/services/preferences/common/preferences';
-import { TerminalExitReason } from 'vs/platform/terminal/common/terminal';
 import { IRemoteAgentService } from 'vs/workbench/services/remote/common/remoteAgentService';
-import { IInstantiationService } from 'vs/platform/instantiation/common/instantiation';
-import { raceTimeout } from 'vs/base/common/async';
 
 const QUICKOPEN_HISTORY_LIMIT_CONFIG = 'task.quickOpen.history';
 const PROBLEM_MATCHER_NEVER_CONFIG = 'task.problemMatchers.neverPrompt';
@@ -223,8 +223,10 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 
 	protected _outputChannel: IOutputChannel;
 	protected readonly _onDidStateChange: Emitter<ITaskEvent>;
-	private _waitForSupportedExecutions: Promise<void>;
+	private _waitForOneSupportedExecution: Promise<void>;
+	private _waitForAllSupportedExecutions: Promise<void>;
 	private _onDidRegisterSupportedExecutions: Emitter<void> = new Emitter();
+	private _onDidRegisterAllSupportedExecutions: Emitter<void> = new Emitter();
 	private _onDidChangeTaskSystemInfo: Emitter<void> = new Emitter();
 	private _willRestart: boolean = false;
 	public onDidChangeTaskSystemInfo: Event<void> = this._onDidChangeTaskSystemInfo.event;
@@ -333,9 +335,12 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 				this._setPersistentTask(e.__task);
 			}
 		}));
-		this._waitForSupportedExecutions = new Promise(resolve => {
+		this._waitForOneSupportedExecution = new Promise(resolve => {
 			once(this._onDidRegisterSupportedExecutions.event)(() => resolve());
 		});
+		this._waitForAllSupportedExecutions = new Promise(resolve => {
+			once(this._onDidRegisterAllSupportedExecutions.event)(() => resolve());
+		});
 		if (this._terminalService.getReconnectedTerminals('Task')?.length) {
 			this._attemptTaskReconnection();
 		} else {
@@ -365,6 +370,9 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 		// update tasks so an incomplete list isn't returned when getWorkspaceTasks is called
 		this._workspaceTasksPromise = undefined;
 		this._onDidRegisterSupportedExecutions.fire();
+		if (custom && shell && process) {
+			this._onDidRegisterAllSupportedExecutions.fire();
+		}
 	}
 
 	private _attemptTaskReconnection(): void {
@@ -2201,7 +2209,12 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 		if (!(await this._trust())) {
 			return new Map();
 		}
-		await this._waitForSupportedExecutions;
+		await this._waitForOneSupportedExecution;
+		if (runSource === TaskRunSource.Reconnect) {
+			await raceTimeout(this._waitForAllSupportedExecutions, 2000, () => {
+				this._logService.warn('Timed out waiting for all supported executions for task reconnection');
+			});
+		}
 		await this._whenTaskSystemReady;
 		if (this._workspaceTasksPromise) {
 			return this._workspaceTasksPromise;
@@ -2878,7 +2891,7 @@ export abstract class AbstractTaskService extends Disposable implements ITaskSer
 	/**
 	 *
 	 * @param tasks - The tasks which need to be filtered
-	 * @param taskGlobsInList - This tells splitPerGroupType to filter out globbed tasks (into defaults)
+	 * @param tasksInList - This tells splitPerGroupType to filter out globbed tasks (into defaults)
 	 * @returns
 	 */
 	private _getDefaultTasks(tasks: Task[], taskGlobsInList: boolean = false): Task[] {