diff --git a/src/Filesystem/Directory.php b/src/Filesystem/Directory.php
index 8ce9162..5f95450 100644
--- a/src/Filesystem/Directory.php
+++ b/src/Filesystem/Directory.php
@@ -38,6 +38,13 @@ public function create(string $path, int $mode = 0777): bool
     public function remove(string $directory): bool
     {
         $directory = realpath($directory);
+
+        // Nothing to remove: the directory does not exist (any more) or is a file.
+        // Both would make the iterator below throw, which is fatal in a destructor.
+        if ($directory === false || !is_dir($directory)) {
+            return false;
+        }
+
         $iterator = new \RecursiveIteratorIterator(
             new \RecursiveDirectoryIterator($directory, \FilesystemIterator::SKIP_DOTS),
             \RecursiveIteratorIterator::CHILD_FIRST
diff --git a/tests/Unit/Command/Extension/UploadExtensionVersionCommandTest.php b/tests/Unit/Command/Extension/UploadExtensionVersionCommandTest.php
index 1e90327..4b83fbf 100644
--- a/tests/Unit/Command/Extension/UploadExtensionVersionCommandTest.php
+++ b/tests/Unit/Command/Extension/UploadExtensionVersionCommandTest.php
@@ -110,6 +110,26 @@ public function transactionDirectoryIsRemovedAfterwards(): void
         self::assertDirectoryDoesNotExist($this->workingDirectory . '/tailor-version-upload');
     }
 
+    #[Test]
+    public function transactionDirectoryRemovalSurvivesAnAlreadyRemovedDirectory(): void
+    {
+        $command = $this->command();
+        $tester = $this->apiTester($command, self::jsonResponse([], 201));
+        $tester->execute($this->uploadArguments());
+
+        // Something removed the transaction directory before the destructor could
+        $transactionPath = $this->workingDirectory . '/tailor-version-upload';
+        foreach ((array)glob($transactionPath . '/*') as $file) {
+            unlink((string)$file);
+        }
+        rmdir($transactionPath);
+
+        unset($command, $tester);
+        gc_collect_cycles();
+
+        self::assertDirectoryDoesNotExist($transactionPath);
+    }
+
     #[Test]
     public function failingRequestReturnsFailure(): void
     {
diff --git a/tests/Unit/Filesystem/DirectoryTest.php b/tests/Unit/Filesystem/DirectoryTest.php
new file mode 100644
index 0000000..a828723
--- /dev/null
+++ b/tests/Unit/Filesystem/DirectoryTest.php
@@ -0,0 +1,63 @@
+<?php
+
+declare(strict_types=1);
+
+/*
+ * This file is part of the TYPO3 project  - inspiring people to share!
+ * (c) 2020 Oliver Bartsch & Benni Mack
+ *
+ * For the full copyright and license information, please view
+ * the LICENSE file that was distributed with this source code.
+ */
+
+namespace TYPO3\Tailor\Tests\Unit\Filesystem;
+
+use PHPUnit\Framework\Attributes\Test;
+use PHPUnit\Framework\TestCase;
+use TYPO3\Tailor\Filesystem\Directory;
+
+class DirectoryTest extends TestCase
+{
+    /** @var string */
+    private $temporaryDirectory = '';
+
+    protected function setUp(): void
+    {
+        $this->temporaryDirectory = sys_get_temp_dir() . '/tailor-test-' . bin2hex(random_bytes(8));
+        mkdir($this->temporaryDirectory, 0777, true);
+    }
+
+    protected function tearDown(): void
+    {
+        if (is_dir($this->temporaryDirectory)) {
+            (new Directory())->remove($this->temporaryDirectory);
+        }
+    }
+
+    #[Test]
+    public function directoryIsRemovedWithItsContent(): void
+    {
+        mkdir($this->temporaryDirectory . '/nested/deeper', 0777, true);
+        file_put_contents($this->temporaryDirectory . '/artefact.zip', 'content');
+        file_put_contents($this->temporaryDirectory . '/nested/deeper/file.txt', 'content');
+
+        self::assertTrue((new Directory())->remove($this->temporaryDirectory));
+        self::assertDirectoryDoesNotExist($this->temporaryDirectory);
+    }
+
+    #[Test]
+    public function removingANonExistingDirectoryReturnsFalse(): void
+    {
+        self::assertFalse((new Directory())->remove($this->temporaryDirectory . '/never-created'));
+    }
+
+    #[Test]
+    public function removingAFileReturnsFalse(): void
+    {
+        $file = $this->temporaryDirectory . '/artefact.zip';
+        file_put_contents($file, 'content');
+
+        self::assertFalse((new Directory())->remove($file));
+        self::assertFileExists($file);
+    }
+}