diff --git a/apps/workflowengine/composer/composer/autoload_classmap.php b/apps/workflowengine/composer/composer/autoload_classmap.php
index 0444cce13e7..52d221fb767 100644
--- a/apps/workflowengine/composer/composer/autoload_classmap.php
+++ b/apps/workflowengine/composer/composer/autoload_classmap.php
@@ -10,6 +10,7 @@ return array(
     'OCA\\WorkflowEngine\\AppInfo\\Application' => $baseDir . '/../lib/AppInfo/Application.php',
     'OCA\\WorkflowEngine\\BackgroundJobs\\Rotate' => $baseDir . '/../lib/BackgroundJobs/Rotate.php',
     'OCA\\WorkflowEngine\\Check\\AbstractStringCheck' => $baseDir . '/../lib/Check/AbstractStringCheck.php',
+    'OCA\\WorkflowEngine\\Check\\Directory' => $baseDir . '/../lib/Check/Directory.php',
     'OCA\\WorkflowEngine\\Check\\FileMimeType' => $baseDir . '/../lib/Check/FileMimeType.php',
     'OCA\\WorkflowEngine\\Check\\FileName' => $baseDir . '/../lib/Check/FileName.php',
     'OCA\\WorkflowEngine\\Check\\FileSize' => $baseDir . '/../lib/Check/FileSize.php',
diff --git a/apps/workflowengine/composer/composer/autoload_static.php b/apps/workflowengine/composer/composer/autoload_static.php
index 0b9ac89ae30..57b569dbc10 100644
--- a/apps/workflowengine/composer/composer/autoload_static.php
+++ b/apps/workflowengine/composer/composer/autoload_static.php
@@ -25,6 +25,7 @@ class ComposerStaticInitWorkflowEngine
         'OCA\\WorkflowEngine\\AppInfo\\Application' => __DIR__ . '/..' . '/../lib/AppInfo/Application.php',
         'OCA\\WorkflowEngine\\BackgroundJobs\\Rotate' => __DIR__ . '/..' . '/../lib/BackgroundJobs/Rotate.php',
         'OCA\\WorkflowEngine\\Check\\AbstractStringCheck' => __DIR__ . '/..' . '/../lib/Check/AbstractStringCheck.php',
+        'OCA\\WorkflowEngine\\Check\\Directory' => __DIR__ . '/..' . '/../lib/Check/Directory.php',
         'OCA\\WorkflowEngine\\Check\\FileMimeType' => __DIR__ . '/..' . '/../lib/Check/FileMimeType.php',
         'OCA\\WorkflowEngine\\Check\\FileName' => __DIR__ . '/..' . '/../lib/Check/FileName.php',
         'OCA\\WorkflowEngine\\Check\\FileSize' => __DIR__ . '/..' . '/../lib/Check/FileSize.php',
diff --git a/apps/workflowengine/lib/Check/Directory.php b/apps/workflowengine/lib/Check/Directory.php
new file mode 100644
index 00000000000..f7b856a95fe
--- /dev/null
+++ b/apps/workflowengine/lib/Check/Directory.php
@@ -0,0 +1,58 @@
+<?php
+
+declare(strict_types=1);
+
+/**
+ * SPDX-FileCopyrightText: 2025 Nextcloud GmbH and Nextcloud contributors
+ * SPDX-License-Identifier: AGPL-3.0-or-later
+ */
+namespace OCA\WorkflowEngine\Check;
+
+use OCA\WorkflowEngine\Entity\File;
+use OCP\IL10N;
+use OCP\WorkflowEngine\IFileCheck;
+
+class Directory extends AbstractStringCheck implements IFileCheck {
+	use TFileCheck;
+
+	/**
+	 * @param IL10N $l
+	 */
+	public function __construct(
+		IL10N $l,
+	) {
+		parent::__construct($l);
+	}
+
+	/**
+	 * @return string
+	 */
+	protected function getActualValue(): string {
+		if ($this->path === null) {
+			return '';
+		}
+		// files/some/path -> some/path
+		return preg_replace('/^files\//', '', pathinfo($this->path, PATHINFO_DIRNAME));
+	}
+
+	/**
+	 * @param string $operator
+	 * @param string $checkValue
+	 * @param string $actualValue
+	 * @return bool
+	 */
+	protected function executeStringCheck($operator, $checkValue, $actualValue) {
+		if ($operator === 'is' || $operator === '!is') {
+			$checkValue = ltrim(rtrim($checkValue, '/'), '/');
+		}
+		return parent::executeStringCheck($operator, $checkValue, $actualValue);
+	}
+
+	public function supportedEntities(): array {
+		return [ File::class ];
+	}
+
+	public function isAvailableForScope(int $scope): bool {
+		return true;
+	}
+}
diff --git a/apps/workflowengine/lib/Manager.php b/apps/workflowengine/lib/Manager.php
index 0f41679789d..27b25a2e752 100644
--- a/apps/workflowengine/lib/Manager.php
+++ b/apps/workflowengine/lib/Manager.php
@@ -8,6 +8,7 @@ namespace OCA\WorkflowEngine;
 
 use Doctrine\DBAL\Exception;
 use OCA\WorkflowEngine\AppInfo\Application;
+use OCA\WorkflowEngine\Check\Directory;
 use OCA\WorkflowEngine\Check\FileMimeType;
 use OCA\WorkflowEngine\Check\FileName;
 use OCA\WorkflowEngine\Check\FileSize;
@@ -692,6 +693,7 @@ class Manager implements IManager {
 	protected function getBuildInChecks(): array {
 		try {
 			return [
+				$this->container->query(Directory::class),
 				$this->container->query(FileMimeType::class),
 				$this->container->query(FileName::class),
 				$this->container->query(FileSize::class),
diff --git a/apps/workflowengine/src/components/Checks/file.js b/apps/workflowengine/src/components/Checks/file.js
index 568efc81cd3..b2d348e4712 100644
--- a/apps/workflowengine/src/components/Checks/file.js
+++ b/apps/workflowengine/src/components/Checks/file.js
@@ -31,6 +31,19 @@ const FileChecks = [
 		validate: stringValidator,
 	},
 
+	{
+		class: 'OCA\\WorkflowEngine\\Check\\Directory',
+		name: t('workflowengine', 'Directory'),
+		operators: stringOrRegexOperators,
+		placeholder: (check) => {
+			if (check.operator === 'matches' || check.operator === '!matches') {
+				return '/^myfolder/.+$/i'
+			}
+			return 'myfolder/subfolder'
+		},
+		validate: stringValidator,
+	},
+
 	{
 		class: 'OCA\\WorkflowEngine\\Check\\FileMimeType',
 		name: t('workflowengine', 'File MIME type'),
diff --git a/apps/workflowengine/tests/Check/DirectoryTest.php b/apps/workflowengine/tests/Check/DirectoryTest.php
new file mode 100644
index 00000000000..6eef082b5e5
--- /dev/null
+++ b/apps/workflowengine/tests/Check/DirectoryTest.php
@@ -0,0 +1,68 @@
+<?php
+
+declare(strict_types=1);
+/**
+ * SPDX-FileCopyrightText: 2025 Nextcloud GmbH and Nextcloud contributors
+ * SPDX-License-Identifier: AGPL-3.0-or-later
+ */
+
+namespace OCA\WorkflowEngine\Tests\Check;
+
+use OCA\WorkflowEngine\Check\Directory;
+use OCA\WorkflowEngine\Entity\File;
+use OCP\Files\Storage\IStorage;
+use OCP\IL10N;
+use Test\TestCase;
+
+class DirectoryTest extends TestCase {
+	/** @var IL10N */
+	private $l10n;
+
+	/** @var IStorage */
+	private $storage;
+
+	/** @var Directory */
+	private $directory;
+
+	protected function setUp(): void {
+		parent::setUp();
+		$this->l10n = $this->createMock(IL10N::class);
+		$this->storage = $this->createMock(IStorage::class);
+		$this->directory = new Directory($this->l10n);
+	}
+
+	/**
+	 * @dataProvider dataProviderCheck
+	 */
+	public function testExecuteStringCheck(string $operator, string $configuredDirectoryPath, string $filePath, bool $expectedResult): void {
+		$this->directory->setFileInfo($this->storage, $filePath);
+
+		$result = $this->directory->executeCheck($operator, $configuredDirectoryPath);
+
+		$this->assertEquals($expectedResult, $result);
+	}
+
+	public function testSupportedEntities(): void {
+		$this->assertSame([File::class], $this->directory->supportedEntities());
+	}
+
+	public function testIsAvailableForScope(): void {
+		$this->assertTrue($this->directory->isAvailableForScope(1));
+	}
+
+	public function dataProviderCheck(): array {
+		return [
+			['is', 'some/path', 'files/some/path/file.txt', true],
+			['is', '/some/path/', 'files/some/path/file.txt', true],
+
+			['!is', 'some/path', 'files/some/path/file.txt', false],
+			['!is', 'some/path/', 'files/someother/path/file.txt', true],
+
+			['matches', '/^some\/path\/.+$/i', 'files/SomE/PATH/subfolder/file.txt', true],
+			['matches', '/some\/path\/.*\/sub2/', 'files/some/path/subfolder1/sub2/anotherfile.pdf', true],
+
+			['!matches', '/some\/path/', 'files/some/path/file.txt', false],
+			['!matches', '/some\/path/', 'files/another/path/file.txt', true],
+		];
+	}
+}
diff --git a/build/psalm-baseline.xml b/build/psalm-baseline.xml
index 596ff92519e..73dfeab49e4 100644
--- a/build/psalm-baseline.xml
+++ b/build/psalm-baseline.xml
@@ -2783,6 +2783,7 @@
       <code><![CDATA[query]]></code>
       <code><![CDATA[query]]></code>
       <code><![CDATA[query]]></code>
+      <code><![CDATA[query]]></code>
     </DeprecatedMethod>
     <InvalidArgument>
       <code><![CDATA[$missingCheck]]></code>