diff --git a/src/applications/auth/data/PhabricatorAuthHighSecurityToken.php b/src/applications/auth/data/PhabricatorAuthHighSecurityToken.php
--- a/src/applications/auth/data/PhabricatorAuthHighSecurityToken.php
+++ b/src/applications/auth/data/PhabricatorAuthHighSecurityToken.php
@@ -1,3 +1,17 @@
 <?php
 
-final class PhabricatorAuthHighSecurityToken extends Phobject {}
+final class PhabricatorAuthHighSecurityToken
+  extends Phobject {
+
+  private $isUnchallengedToken = false;
+
+  public function setIsUnchallengedToken($is_unchallenged_token) {
+    $this->isUnchallengedToken = $is_unchallenged_token;
+    return $this;
+  }
+
+  public function getIsUnchallengedToken() {
+    return $this->isUnchallengedToken;
+  }
+
+}
diff --git a/src/applications/auth/engine/PhabricatorAuthSessionEngine.php b/src/applications/auth/engine/PhabricatorAuthSessionEngine.php
--- a/src/applications/auth/engine/PhabricatorAuthSessionEngine.php
+++ b/src/applications/auth/engine/PhabricatorAuthSessionEngine.php
@@ -493,7 +493,8 @@
     // adds an auth factor, existing sessions won't get a free pass into hisec,
     // since they never actually got marked as hisec.
     if (!$factors) {
-      return $this->issueHighSecurityToken($session, true);
+      return $this->issueHighSecurityToken($session, true)
+        ->setIsUnchallengedToken(true);
     }
 
     $this->request = $request;
diff --git a/src/applications/transactions/editor/PhabricatorApplicationTransactionEditor.php b/src/applications/transactions/editor/PhabricatorApplicationTransactionEditor.php
--- a/src/applications/transactions/editor/PhabricatorApplicationTransactionEditor.php
+++ b/src/applications/transactions/editor/PhabricatorApplicationTransactionEditor.php
@@ -5152,12 +5152,14 @@
           'an MFA check.'));
     }
 
-    id(new PhabricatorAuthSessionEngine())
+    $token = id(new PhabricatorAuthSessionEngine())
       ->setWorkflowKey($workflow_key)
       ->requireHighSecurityToken($actor, $request, $cancel_uri);
 
-    foreach ($xactions as $xaction) {
-      $xaction->setIsMFATransaction(true);
+    if (!$token->getIsUnchallengedToken()) {
+      foreach ($xactions as $xaction) {
+        $xaction->setIsMFATransaction(true);
+      }
     }
   }