diff --git a/resources/sql/autopatches/20220912.fileattachment.01.delete.sql b/resources/sql/autopatches/20220912.fileattachment.01.delete.sql
new file mode 100644
--- /dev/null
+++ b/resources/sql/autopatches/20220912.fileattachment.01.delete.sql
@@ -0,0 +1,6 @@
+USE {$NAMESPACE}_file;
+  DELETE FROM file_attachment
+  WHERE NOT EXISTS
+  (SELECT *
+    FROM file
+    WHERE phid=file_attachment.filePHID)
\ No newline at end of file
diff --git a/src/__phutil_library_map__.php b/src/__phutil_library_map__.php
--- a/src/__phutil_library_map__.php
+++ b/src/__phutil_library_map__.php
@@ -3457,6 +3457,7 @@
     'PhabricatorFileAltTextTransaction' => 'applications/files/xaction/PhabricatorFileAltTextTransaction.php',
     'PhabricatorFileAttachment' => 'applications/files/storage/PhabricatorFileAttachment.php',
     'PhabricatorFileAttachmentQuery' => 'applications/files/query/PhabricatorFileAttachmentQuery.php',
+    'PhabricatorFileAttachmentsDestructionEngineExtension' => 'applications/files/engineextension/PhabricatorFilesAttachmentsDestructionEngineExtension.php',
     'PhabricatorFileBundleLoader' => 'applications/files/query/PhabricatorFileBundleLoader.php',
     'PhabricatorFileChunk' => 'applications/files/storage/PhabricatorFileChunk.php',
     'PhabricatorFileChunkIterator' => 'applications/files/engine/PhabricatorFileChunkIterator.php',
@@ -9918,6 +9919,7 @@
       'PhabricatorExtendedPolicyInterface',
     ),
     'PhabricatorFileAttachmentQuery' => 'PhabricatorCursorPagedPolicyAwareQuery',
+    'PhabricatorFileAttachmentsDestructionEngineExtension' => 'PhabricatorDestructionEngineExtension',
     'PhabricatorFileBundleLoader' => 'Phobject',
     'PhabricatorFileChunk' => array(
       'PhabricatorFileDAO',
diff --git a/src/applications/files/engineextension/PhabricatorFilesAttachmentsDestructionEngineExtension.php b/src/applications/files/engineextension/PhabricatorFilesAttachmentsDestructionEngineExtension.php
new file mode 100644
--- /dev/null
+++ b/src/applications/files/engineextension/PhabricatorFilesAttachmentsDestructionEngineExtension.php
@@ -0,0 +1,28 @@
+<?php
+
+final class PhabricatorFileAttachmentsDestructionEngineExtension
+  extends PhabricatorDestructionEngineExtension {
+
+  const EXTENSIONKEY = 'attachments';
+
+  public function getExtensionName() {
+    return pht('File Attachments');
+  }
+
+  public function canDestroyObject(
+    PhabricatorDestructionEngine $engine,
+    $object) {
+    return ($object instanceof PhabricatorFile);
+  }
+
+  public function destroyObject(
+    PhabricatorDestructionEngine $engine,
+    $object) {
+    $file_phid = $object->getPHID();
+    $attachments = id(new PhabricatorFileAttachmentQuery())
+      ->setViewer(PhabricatorUser::getOmnipotentUser())
+      ->withFilePHIDs(array($file_phid))
+      ->execute();
+    mpull($attachments, 'delete');
+  }
+}
\ No newline at end of file