diff --git a/lib/AppInfo/Application.php b/lib/AppInfo/Application.php
index 74297db3..3bb0d957 100644
--- a/lib/AppInfo/Application.php
+++ b/lib/AppInfo/Application.php
@@ -92,6 +92,7 @@ public function register(IRegistrationContext $context): void {
 		$context->registerEventListener(TaskSuccessfulEvent::class, TaskSuccessfulListener::class);
 		$context->registerEventListener(TaskFailedEvent::class, TaskFailedListener::class);
 		$context->registerEventListener(TaskSuccessfulEvent::class, ChattyLLMTaskListener::class);
+		$context->registerEventListener(TaskFailedEvent::class, ChattyLLMTaskListener::class);
 		$context->registerEventListener(TaskSuccessfulEvent::class, FileActionTaskSuccessfulListener::class);
 		$context->registerEventListener(TaskSuccessfulEvent::class, NewFileMenuTaskSuccessfulListener::class);
 		$context->registerEventListener(TaskFailedEvent::class, FileActionTaskFailedListener::class);
diff --git a/lib/Listener/ChattyLLMTaskListener.php b/lib/Listener/ChattyLLMTaskListener.php
index 5cdc3882..cbb7e4cb 100644
--- a/lib/Listener/ChattyLLMTaskListener.php
+++ b/lib/Listener/ChattyLLMTaskListener.php
@@ -13,15 +13,17 @@
 use OCA\Assistant\Db\ChattyLLM\Message;
 use OCA\Assistant\Db\ChattyLLM\MessageMapper;
 use OCA\Assistant\Db\ChattyLLM\SessionMapper;
+use OCA\Assistant\Service\NotificationService;
 use OCA\Assistant\Service\TaskProcessingService;
 use OCP\EventDispatcher\Event;
 use OCP\EventDispatcher\IEventListener;
+use OCP\TaskProcessing\Events\TaskFailedEvent;
 use OCP\TaskProcessing\Events\TaskSuccessfulEvent;
 use OCP\TaskProcessing\Task;
 use Psr\Log\LoggerInterface;
 
 /**
- * @template-implements IEventListener<TaskSuccessfulEvent>
+ * @template-implements IEventListener<TaskSuccessfulEvent|TaskFailedEvent>
  */
 class ChattyLLMTaskListener implements IEventListener {
 
@@ -30,10 +32,26 @@ public function __construct(
 		private SessionMapper $sessionMapper,
 		private TaskProcessingService $taskProcessingService,
 		private LoggerInterface $logger,
+		private NotificationService $notificationService,
 	) {
 	}
 
 	public function handle(Event $event): void {
+		if ($event instanceof TaskFailedEvent) {
+			$task = $event->getTask();
+			$customId = $task->getCustomId();
+			if (preg_match('/^chatty-llm:(\d+)/', $customId, $matches)) {
+				$sessionId = (int)$matches[1];
+				$session = $this->sessionMapper->getUserSession($task->getUserId(), $sessionId);
+				$assignmentId = $session->getAssignmentId();
+				if ($assignmentId !== null) {
+					$this->notificationService->sendAssignmentNotification(
+						$task->getUserId(), $task, $session
+					);
+				}
+			}
+			return;
+		}
 		if (!($event instanceof TaskSuccessfulEvent)) {
 			return;
 		}
@@ -127,6 +145,13 @@ public function handle(Event $event): void {
 			// Set flag that the conversation summary needs to be regenerated
 			$session->setIsSummaryUpToDate(false);
 
+			$assignmentId = $session->getAssignmentId();
+			if ($assignmentId !== null) {
+				$this->notificationService->sendAssignmentNotification(
+					$task->getUserId(), $task, $session
+				);
+			}
+
 			$this->sessionMapper->update($session);
 		}
 	}
diff --git a/lib/Notification/Notifier.php b/lib/Notification/Notifier.php
index d1695d13..2f38de2a 100644
--- a/lib/Notification/Notifier.php
+++ b/lib/Notification/Notifier.php
@@ -338,6 +338,81 @@ public function prepare(INotification $notification, string $languageCode): INot
 
 				return $notification;
 
+			case 'assignment_approval_pending':
+				$subject = $l->t('Assignment run pending review');
+
+				$iconUrl = $this->url->getAbsoluteURL($this->url->imagePath(Application::APP_ID, 'app-dark.svg'));
+
+				$message = $l->t('"%s" awaits your review before continuing.', [$params['sessionTitle']]);
+
+				$notification
+					->setParsedSubject($subject)
+					->setParsedMessage($message)
+					// TODO: link directly to assignment
+					->setLink($this->url->linkToRouteAbsolute(Application::APP_ID . '.assistant.getAssistantStandalonePage', ['sessionId' => $params['sessionId']]))
+					->setIcon($iconUrl);
+
+				$actionLabel = $l->t('View assignment');
+				$action = $notification->createAction();
+				$action->setLabel($actionLabel)
+					->setParsedLabel($actionLabel)
+					->setLink($notification->getLink(), IAction::TYPE_WEB)
+					->setPrimary(true);
+
+				$notification->addParsedAction($action);
+
+				return $notification;
+
+			case 'assignment_successful':
+				$subject = $l->t('Assignment succeeded');
+
+				$iconUrl = $this->url->getAbsoluteURL($this->url->imagePath(Application::APP_ID, 'app-dark.svg'));
+
+				$message = $l->t('"%s" was run successfully.', [$params['sessionTitle']]);
+
+				$notification
+					->setParsedSubject($subject)
+					->setParsedMessage($message)
+					// TODO: link directly to assignment
+					->setLink($this->url->linkToRouteAbsolute(Application::APP_ID . '.assistant.getAssistantStandalonePage', ['sessionId' => $params['sessionId']]))
+					->setIcon($iconUrl);
+
+				$actionLabel = $l->t('View assignment result');
+				$action = $notification->createAction();
+				$action->setLabel($actionLabel)
+					->setParsedLabel($actionLabel)
+					->setLink($notification->getLink(), IAction::TYPE_WEB)
+					->setPrimary(true);
+
+				$notification->addParsedAction($action);
+
+				return $notification;
+
+			case 'assignment_failure':
+				$subject = $l->t('Assignment failed');
+
+				$iconUrl = $this->url->getAbsoluteURL($this->url->imagePath(Application::APP_ID, 'app-dark.svg'));
+
+				$message = $l->t('"%s" failed to run.', [$params['sessionTitle']]);
+
+				$notification
+					->setParsedSubject($subject)
+					->setParsedMessage($message)
+					// TODO: link directly to assignment
+					->setLink($this->url->linkToRouteAbsolute(Application::APP_ID . '.assistant.getAssistantStandalonePage', ['sessionId' => $params['sessionId']]))
+					->setIcon($iconUrl);
+
+				$actionLabel = $l->t('View assignment result');
+				$action = $notification->createAction();
+				$action->setLabel($actionLabel)
+					->setParsedLabel($actionLabel)
+					->setLink($notification->getLink(), IAction::TYPE_WEB)
+					->setPrimary(true);
+
+				$notification->addParsedAction($action);
+
+				return $notification;
+
 			default:
 				// Unknown subject => Unknown notification => throw
 				throw new InvalidArgumentException();
diff --git a/lib/Service/NotificationService.php b/lib/Service/NotificationService.php
index 82a59664..5fc3ab14 100644
--- a/lib/Service/NotificationService.php
+++ b/lib/Service/NotificationService.php
@@ -9,6 +9,7 @@
 
 use DateTime;
 use OCA\Assistant\AppInfo\Application;
+use OCA\Assistant\Db\ChattyLLM\Session;
 use OCP\IURLGenerator;
 use OCP\Notification\IManager as INotificationManager;
 use OCP\TaskProcessing\Task;
@@ -133,4 +134,34 @@ public function sendNewImageFileNotification(
 
 		$manager->notify($notification);
 	}
+
+	public function sendAssignmentNotification(?string $userId, Task $task, Session $session): void {
+		if ($userId === null) {
+			return;
+		}
+		$manager = $this->notificationManager;
+		$notification = $manager->createNotification();
+
+		$taskSuccessful = $task->getStatus() === Task::STATUS_SUCCESSFUL;
+		$pendingActions = $session->getAgencyPendingActions();
+
+		$params = [
+			'sessionId' => (string)$session->getId(),
+			'sessionTitle' => $session->getTitle(),
+		];
+
+		$subject = $taskSuccessful
+			? ($pendingActions === null
+			  ? 'assignment_successful'
+			  : 'assignment_approval_pending')
+			: 'assignment_failure';
+
+		$notification->setApp(Application::APP_ID)
+			->setUser($userId)
+			->setDateTime(new DateTime())
+			->setSubject($subject, $params)
+			->setObject('session', (string)$session->getId());
+
+		$manager->notify($notification);
+	}
 }