diff --git a/src/applications/herald/controller/HeraldTestConsoleController.php b/src/applications/herald/controller/HeraldTestConsoleController.php
--- a/src/applications/herald/controller/HeraldTestConsoleController.php
+++ b/src/applications/herald/controller/HeraldTestConsoleController.php
@@ -260,24 +260,48 @@
     $query = PhabricatorApplicationTransactionQuery::newQueryForObject(
       $object);
 
-    $xactions = $query
+    $query
       ->withObjectPHIDs(array($object->getPHID()))
-      ->setViewer($viewer)
-      ->setLimit(100)
-      ->execute();
+      ->setViewer($viewer);
+
+    $xactions = new PhabricatorQueryIterator($query);
 
     $applied = array();
 
-    // Pick the most recent group of transactions. This may not be exactly the
-    // same as what Herald acted on: for example, we may select a single group
-    // of transactions here which were really applied across two or more edits.
-    // Since this is relatively rare and we show you what we picked, it's okay
-    // that we just do roughly the right thing.
+    $recent_id = null;
+    $hard_limit = 1000;
     foreach ($xactions as $xaction) {
-      if (!$xaction->shouldDisplayGroupWith($applied)) {
+      $group_id = $xaction->getTransactionGroupID();
+
+      // If this is the first transaction, save the group ID: we want to
+      // select all transactions in the same group.
+      if (!$applied) {
+        $recent_id = $group_id;
+        if ($recent_id === null) {
+          // If the first transaction has no group ID, it is likely an older
+          // transaction from before the introduction of group IDs. In this
+          // case, select only the most recent transaction and bail out.
+          $applied[] = $xaction;
+          break;
+        }
+      }
+
+      // If this transaction is from a different transaction group, we've
+      // found all the transactions applied in the most recent group.
+      if ($group_id !== $recent_id) {
         break;
       }
+
       $applied[] = $xaction;
+
+      if (count($applied) > $hard_limit) {
+        throw new Exception(
+          pht(
+            'This object ("%s") has more than %s transactions in its most '.
+            'recent transaction group; this is too many.',
+            $object->getPHID(),
+            new PhutilNumber($hard_limit)));
+      }
     }
 
     return $applied;
diff --git a/src/applications/transactions/conduit/TransactionSearchConduitAPIMethod.php b/src/applications/transactions/conduit/TransactionSearchConduitAPIMethod.php
--- a/src/applications/transactions/conduit/TransactionSearchConduitAPIMethod.php
+++ b/src/applications/transactions/conduit/TransactionSearchConduitAPIMethod.php
@@ -260,6 +260,13 @@
         }
       }
 
+      $group_id = $xaction->getTransactionGroupID();
+      if (!strlen($group_id)) {
+        $group_id = null;
+      } else {
+        $group_id = (string)$group_id;
+      }
+
       $data[] = array(
         'id' => (int)$xaction->getID(),
         'phid' => (string)$xaction->getPHID(),
@@ -268,6 +275,7 @@
         'objectPHID' => (string)$xaction->getObjectPHID(),
         'dateCreated' => (int)$xaction->getDateCreated(),
         'dateModified' => (int)$xaction->getDateModified(),
+        'groupID' => $group_id,
         'comments' => $comment_data,
         'fields' => $fields,
       );
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
@@ -1162,6 +1162,8 @@
         throw $ex;
       }
 
+      $group_id = Filesystem::readRandomCharacters(32);
+
       foreach ($xactions as $xaction) {
         if ($was_locked) {
           $is_override = $this->isLockOverrideTransaction($xaction);
@@ -1171,6 +1173,8 @@
         }
 
         $xaction->setObjectPHID($object->getPHID());
+        $xaction->setTransactionGroupID($group_id);
+
         if ($xaction->getComment()) {
           $xaction->setPHID($xaction->generatePHID());
           $comment_editor->applyEdit($xaction, $xaction->getComment());
diff --git a/src/applications/transactions/storage/PhabricatorApplicationTransaction.php b/src/applications/transactions/storage/PhabricatorApplicationTransaction.php
--- a/src/applications/transactions/storage/PhabricatorApplicationTransaction.php
+++ b/src/applications/transactions/storage/PhabricatorApplicationTransaction.php
@@ -177,6 +177,14 @@
     return (bool)$this->getMetadataValue('core.lock-override', false);
   }
 
+  public function setTransactionGroupID($group_id) {
+    return $this->setMetadataValue('core.groupID', $group_id);
+  }
+
+  public function getTransactionGroupID() {
+    return $this->getMetadataValue('core.groupID', null);
+  }
+
   public function attachComment(
     PhabricatorApplicationTransactionComment $comment) {
     $this->comment = $comment;