diff --git a/src/applications/files/transform/PhabricatorFileTransform.php b/src/applications/files/transform/PhabricatorFileTransform.php
--- a/src/applications/files/transform/PhabricatorFileTransform.php
+++ b/src/applications/files/transform/PhabricatorFileTransform.php
@@ -27,6 +27,22 @@
     return $this->getDefaultTransform($file);
   }
 
+  /**
+   * Wrapper of executeTransform() that also persists the relationship
+   * between the original file and the transform.
+   */
+  public function executeTransformExplicit(PhabricatorFile $file) {
+    $xform = $this->executeTransform($file);
+
+    id(new PhabricatorTransformedFile())
+      ->setOriginalPHID($file->getPHID())
+      ->setTransformedPHID($xform->getPHID())
+      ->setTransform($this->getTransformKey())
+      ->save();
+
+    return $xform;
+  }
+
   public static function getAllTransforms() {
     return id(new PhutilClassMapQuery())
       ->setAncestorClass(__CLASS__)
diff --git a/src/applications/maniphest/xaction/ManiphestTaskCoverImageTransaction.php b/src/applications/maniphest/xaction/ManiphestTaskCoverImageTransaction.php
--- a/src/applications/maniphest/xaction/ManiphestTaskCoverImageTransaction.php
+++ b/src/applications/maniphest/xaction/ManiphestTaskCoverImageTransaction.php
@@ -30,14 +30,7 @@
     // Generate an image transformation, usually smaller (orphan now).
     $xform_key = PhabricatorFileThumbnailTransform::TRANSFORM_WORKCARD;
     $xform = PhabricatorFileTransform::getTransformByKey($xform_key)
-      ->executeTransform($file);
-
-    // Make that image transformation non-orphan.
-    id(new PhabricatorTransformedFile())
-      ->setOriginalPHID($file_phid)
-      ->setTransformedPHID($xform->getPHID())
-      ->setTransform($xform_key)
-      ->save();
+      ->executeTransformExplicit($file);
 
     $object->setProperty('cover.filePHID', $file->getPHID());
     $object->setProperty('cover.thumbnailPHID', $xform->getPHID());
diff --git a/src/applications/people/controller/PhabricatorPeopleProfilePictureController.php b/src/applications/people/controller/PhabricatorPeopleProfilePictureController.php
--- a/src/applications/people/controller/PhabricatorPeopleProfilePictureController.php
+++ b/src/applications/people/controller/PhabricatorPeopleProfilePictureController.php
@@ -69,7 +69,7 @@
         } else {
           $xform = PhabricatorFileTransform::getTransformByKey(
             PhabricatorFileThumbnailTransform::TRANSFORM_PROFILE);
-          $xformed = $xform->executeTransform($file);
+          $xformed = $xform->executeTransformExplicit($file);
         }
       }