diff --git a/resources/sql/autopatches/20230917.fileattachment.01.delete.sql b/resources/sql/autopatches/20230917.fileattachment.01.delete.sql
new file mode 100644
--- /dev/null
+++ b/resources/sql/autopatches/20230917.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)
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
@@ -3456,6 +3456,7 @@
     'PhabricatorFileAES256StorageFormat' => 'applications/files/format/PhabricatorFileAES256StorageFormat.php',
     'PhabricatorFileAltTextTransaction' => 'applications/files/xaction/PhabricatorFileAltTextTransaction.php',
     'PhabricatorFileAttachment' => 'applications/files/storage/PhabricatorFileAttachment.php',
+    'PhabricatorFileAttachmentDestructionEngineExtension' => 'applications/files/engineextension/PhabricatorFileAttachmentDestructionEngineExtension.php',
     'PhabricatorFileAttachmentQuery' => 'applications/files/query/PhabricatorFileAttachmentQuery.php',
     'PhabricatorFileBundleLoader' => 'applications/files/query/PhabricatorFileBundleLoader.php',
     'PhabricatorFileChunk' => 'applications/files/storage/PhabricatorFileChunk.php',
@@ -9917,6 +9918,7 @@
       'PhabricatorPolicyInterface',
       'PhabricatorExtendedPolicyInterface',
     ),
+    'PhabricatorFileAttachmentDestructionEngineExtension' => 'PhabricatorDestructionEngineExtension',
     'PhabricatorFileAttachmentQuery' => 'PhabricatorCursorPagedPolicyAwareQuery',
     'PhabricatorFileBundleLoader' => 'Phobject',
     'PhabricatorFileChunk' => array(
diff --git a/src/applications/files/engineextension/PhabricatorFileAttachmentDestructionEngineExtension.php b/src/applications/files/engineextension/PhabricatorFileAttachmentDestructionEngineExtension.php
new file mode 100644
--- /dev/null
+++ b/src/applications/files/engineextension/PhabricatorFileAttachmentDestructionEngineExtension.php
@@ -0,0 +1,22 @@
+<?php
+
+final class PhabricatorFileAttachmentDestructionEngineExtension
+  extends PhabricatorDestructionEngineExtension {
+
+  const EXTENSIONKEY = 'file.attachments';
+
+  public function getExtensionName() {
+    return pht('File Attachments');
+  }
+
+  public function destroyObject(
+    PhabricatorDestructionEngine $engine,
+    $object) {
+    $attachments = id(new PhabricatorFileAttachment())->loadAllWhere(
+      'objectPHID = %s',
+      $object->getPHID());
+    foreach ($attachments as $attachment) {
+      $attachment->delete();
+    }
+  }
+}
diff --git a/src/applications/files/storage/PhabricatorFile.php b/src/applications/files/storage/PhabricatorFile.php
--- a/src/applications/files/storage/PhabricatorFile.php
+++ b/src/applications/files/storage/PhabricatorFile.php
@@ -1705,6 +1705,14 @@
     PhabricatorDestructionEngine $engine) {
 
     $this->openTransaction();
+
+      $attachments = id(new PhabricatorFileAttachment())->loadAllWhere(
+        'filePHID = %s',
+        $this->getPHID());
+      foreach ($attachments as $attachment) {
+        $attachment->delete();
+      }
+
       $this->delete();
     $this->saveTransaction();
   }