diff --git a/lib/Cron/Cleanup.php b/lib/Cron/Cleanup.php
index 4b2d0e9d337..ce52af86d16 100644
--- a/lib/Cron/Cleanup.php
+++ b/lib/Cron/Cleanup.php
@@ -18,6 +18,7 @@
 use OCA\Text\Service\SessionService;
 use OCP\AppFramework\Utility\ITimeFactory;
 use OCP\BackgroundJob\TimedJob;
+use OCP\Files\NotPermittedException;
 use OCP\Server;
 use Psr\Log\LoggerInterface;
 
@@ -43,9 +44,15 @@ protected function run($argument): void {
 			try {
 				$this->documentService->resetDocument($document->getId());
 			} catch (DocumentHasUnsavedChangesException) {
+				// The saved file may not reference attachments that are only used in unsaved steps yet
+				continue;
 			}
 			$setupManager->tearDown();
-			$this->attachmentService->cleanupAttachments($document->getId());
+			try {
+				$this->attachmentService->cleanupAttachments($document->getId());
+			} catch (NotPermittedException $e) {
+				$this->logger->warning('Could not clean up attachments of file ' . $document->getId() . ', deleting is not permitted', ['exception' => $e]);
+			}
 		}
 
 		$this->logger->debug('Run cleanup job for text sessions');
diff --git a/tests/unit/CleanupTest.php b/tests/unit/CleanupTest.php
new file mode 100644
index 00000000000..7a78d1b282f
--- /dev/null
+++ b/tests/unit/CleanupTest.php
@@ -0,0 +1,104 @@
+<?php
+
+/**
+ * SPDX-FileCopyrightText: 2026 Nextcloud GmbH and Nextcloud contributors
+ * SPDX-License-Identifier: AGPL-3.0-or-later
+ */
+
+namespace OCA\Text\Tests;
+
+use OCA\Text\Cron\Cleanup;
+use OCA\Text\Db\Document;
+use OCA\Text\Exception\DocumentHasUnsavedChangesException;
+use OCA\Text\Service\AttachmentService;
+use OCA\Text\Service\DocumentService;
+use OCA\Text\Service\SessionService;
+use OCP\AppFramework\Utility\ITimeFactory;
+use OCP\Files\IFilenameValidator;
+use OCP\Files\IMimeTypeDetector;
+use OCP\Files\IRootFolder;
+use OCP\Files\NotPermittedException;
+use OCP\FilesMetadata\IFilesMetadataManager;
+use OCP\IPreview;
+use OCP\ISession;
+use OCP\IURLGenerator;
+use OCP\Share\IManager;
+use Psr\Log\LoggerInterface;
+
+class CleanupTest extends \PHPUnit\Framework\TestCase {
+	private Cleanup $cleanup;
+	private Document $document;
+	private DocumentService $documentService;
+	private SessionService $sessionService;
+	private IRootFolder $rootFolder;
+	private LoggerInterface $logger;
+
+	public function setUp(): void {
+		$this->document = Document::fromRow([
+			'id' => 123,
+			'last_saved_version_time' => 1000,
+		]);
+		$this->documentService = $this->createMock(DocumentService::class);
+		$this->rootFolder = $this->createMock(IRootFolder::class);
+		$attachmentService = new AttachmentService(
+			$this->rootFolder,
+			$this->createMock(IManager::class),
+			$this->createMock(IPreview::class),
+			$this->createMock(IMimeTypeDetector::class),
+			$this->createMock(IURLGenerator::class),
+			$this->createMock(IFilenameValidator::class),
+			$this->createMock(IFilesMetadataManager::class),
+			$this->createMock(ISession::class),
+		);
+		$this->sessionService = $this->createMock(SessionService::class);
+		$this->logger = $this->createMock(LoggerInterface::class);
+		$this->documentService->expects(self::once())
+			->method('getAllWithNoActiveSession')
+			->willReturn((function (): \Generator {
+				yield $this->document;
+			})());
+		$this->cleanup = new class($this->createMock(ITimeFactory::class), $this->sessionService, $this->documentService, $attachmentService, $this->logger) extends Cleanup {
+			public function run($argument): void {
+				parent::run($argument);
+			}
+		};
+	}
+
+	private function expectRemainingCleanupSteps(): void {
+		$this->sessionService->expects(self::once())->method('removeInactiveSessionsWithoutSteps');
+		$this->sessionService->expects(self::once())->method('removeOldSessions');
+		$this->sessionService->expects(self::once())->method('removeOrphanedSteps');
+		$this->documentService->expects(self::once())->method('cleanupOldDocumentsFolders');
+	}
+
+	public function testCleansAttachmentsOfResetDocument(): void {
+		$this->documentService->expects(self::once())->method('resetDocument')->with(123);
+		$this->rootFolder->expects(self::once())
+			->method('getFirstNodeById')->with(123)
+			->willReturn(null);
+		$this->expectRemainingCleanupSteps();
+
+		$this->cleanup->run([]);
+	}
+
+	public function testSkipsAttachmentCleanupForUnsavedChanges(): void {
+		$this->documentService->expects(self::once())
+			->method('resetDocument')->with(123)
+			->willThrowException(new DocumentHasUnsavedChangesException());
+		$this->rootFolder->expects(self::never())->method('getFirstNodeById');
+		$this->expectRemainingCleanupSteps();
+
+		$this->cleanup->run([]);
+	}
+
+	public function testNotPermittedCleanupIsLoggedAndJobContinues(): void {
+		$this->documentService->expects(self::once())->method('resetDocument')->with(123);
+		$this->rootFolder->expects(self::once())
+			->method('getFirstNodeById')->with(123)
+			->willThrowException(new NotPermittedException());
+		$this->logger->expects(self::once())->method('warning');
+		$this->expectRemainingCleanupSteps();
+
+		$this->cleanup->run([]);
+	}
+}