diff --git a/src/applications/auth/controller/PhabricatorAuthRegisterController.php b/src/applications/auth/controller/PhabricatorAuthRegisterController.php
--- a/src/applications/auth/controller/PhabricatorAuthRegisterController.php
+++ b/src/applications/auth/controller/PhabricatorAuthRegisterController.php
@@ -706,7 +706,7 @@
 
     $xform = PhabricatorFileTransform::getTransformByKey(
       PhabricatorFileThumbnailTransform::TRANSFORM_PROFILE);
-    return $xform->executeTransform($file);
+    return $xform->executeTransformExplicit($file);
   }
 
   protected function renderError($message) {
diff --git a/src/applications/conpherence/controller/ConpherenceRoomPictureController.php b/src/applications/conpherence/controller/ConpherenceRoomPictureController.php
--- a/src/applications/conpherence/controller/ConpherenceRoomPictureController.php
+++ b/src/applications/conpherence/controller/ConpherenceRoomPictureController.php
@@ -66,7 +66,7 @@
         } else {
           $xform = PhabricatorFileTransform::getTransformByKey(
             PhabricatorFileThumbnailTransform::TRANSFORM_PROFILE);
-          $xformed = $xform->executeTransform($file);
+          $xformed = $xform->executeTransformExplicit($file);
         }
       }
 
diff --git a/src/applications/diffusion/controller/DiffusionRepositoryProfilePictureController.php b/src/applications/diffusion/controller/DiffusionRepositoryProfilePictureController.php
--- a/src/applications/diffusion/controller/DiffusionRepositoryProfilePictureController.php
+++ b/src/applications/diffusion/controller/DiffusionRepositoryProfilePictureController.php
@@ -67,7 +67,7 @@
         } else {
           $xform = PhabricatorFileTransform::getTransformByKey(
             PhabricatorFileThumbnailTransform::TRANSFORM_PROFILE);
-          $xformed = $xform->executeTransform($file);
+          $xformed = $xform->executeTransformExplicit($file);
         }
       }
 
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 +27,30 @@
     return $this->getDefaultTransform($file);
   }
 
+  /**
+   * Wrapper of executeTransform() that also persists the relationship
+   * between the original file and the transform, if it has sense to do so.
+   */
+  public function executeTransformExplicit(PhabricatorFile $file) {
+    // This can be NULL.
+    $xform = $this->executeTransform($file);
+
+    // Connect the original file to its transform, if any.
+    // Skip transforms that are derived from a builtin as cautionary measure:
+    //  - Builtins may have a lot of transforms. We don't know if the UX scales.
+    //    Example page: /file/transforms/1/
+    //  - Tracking builtins gives unclear benefits.
+    if ($xform && !$file->isBuiltin()) {
+      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);
         }
       }
 
diff --git a/src/applications/phame/controller/blog/PhameBlogProfilePictureController.php b/src/applications/phame/controller/blog/PhameBlogProfilePictureController.php
--- a/src/applications/phame/controller/blog/PhameBlogProfilePictureController.php
+++ b/src/applications/phame/controller/blog/PhameBlogProfilePictureController.php
@@ -66,7 +66,7 @@
         } else {
           $xform = PhabricatorFileTransform::getTransformByKey(
             PhabricatorFileThumbnailTransform::TRANSFORM_PROFILE);
-          $xformed = $xform->executeTransform($file);
+          $xformed = $xform->executeTransformExplicit($file);
         }
       }
 
diff --git a/src/applications/phortune/controller/merchant/PhortuneMerchantPictureController.php b/src/applications/phortune/controller/merchant/PhortuneMerchantPictureController.php
--- a/src/applications/phortune/controller/merchant/PhortuneMerchantPictureController.php
+++ b/src/applications/phortune/controller/merchant/PhortuneMerchantPictureController.php
@@ -56,7 +56,7 @@
         } else {
           $xform = PhabricatorFileTransform::getTransformByKey(
             PhabricatorFileThumbnailTransform::TRANSFORM_PROFILE);
-          $xformed = $xform->executeTransform($file);
+          $xformed = $xform->executeTransformExplicit($file);
         }
       }
 
diff --git a/src/applications/project/controller/PhabricatorProjectEditPictureController.php b/src/applications/project/controller/PhabricatorProjectEditPictureController.php
--- a/src/applications/project/controller/PhabricatorProjectEditPictureController.php
+++ b/src/applications/project/controller/PhabricatorProjectEditPictureController.php
@@ -68,7 +68,7 @@
         } else {
           $xform = PhabricatorFileTransform::getTransformByKey(
             PhabricatorFileThumbnailTransform::TRANSFORM_PROFILE);
-          $xformed = $xform->executeTransform($file);
+          $xformed = $xform->executeTransformExplicit($file);
         }
       }