diff --git a/app/src/Lib/Traits/EntityMetaTrait.php b/app/src/Lib/Traits/EntityMetaTrait.php
index 5cb4c3b13..bd8d7ddf3 100644
--- a/app/src/Lib/Traits/EntityMetaTrait.php
+++ b/app/src/Lib/Traits/EntityMetaTrait.php
@@ -62,7 +62,8 @@ public function isProbablyThisArray(array $data): bool {
 
     foreach($data as $field => $value) {
       if((!isset($this->$field) && !empty($value))   // Value in $data but not $entity
-         || (isset($this->$field) && empty($value))  // Value in $entity but not $data
+         || (isset($this->$field) && empty($value)   // Value in $entity but not $data
+             && !empty($this->$field))                // ... and $entity is not falsey
          || (isset($this->$field) && $this->$field != $value)) {  // Values don't match
         // Not a match
         $match = false;
diff --git a/app/src/Model/Table/PipelinesTable.php b/app/src/Model/Table/PipelinesTable.php
index c5df4f4dd..32f088a1d 100644
--- a/app/src/Model/Table/PipelinesTable.php
+++ b/app/src/Model/Table/PipelinesTable.php
@@ -418,6 +418,14 @@ protected function duplicateFilterEntityData($entity): array {
       $newdata['status']
     );
 
+    // Timestamps are FrozenTime objects in the entity data, and is_scalar
+    // will filter them out, so convert them to strings
+    foreach(['valid_from', 'valid_through'] as $attr) {
+      if(!empty($entity->$attr)) {
+        $newdata[$attr] = $entity->$attr->i18nFormat('yyyy-MM-dd HH:mm:ss');
+      }
+    }
+
     // This will remove anything that isn't stringy
     return array_filter($newdata, 'is_scalar');
   }
@@ -1269,14 +1277,20 @@ protected function syncExternalIdentity(
               // $arecord should include the associated models, so we don't need
               // to do any special handling for them.
 
+              $associated = [];
+
+              if($model == 'ExternalIdentityRoles') {
+                $associated = ['Addresses', 'AdHocAttributes', 'TelephoneNumbers'];
+              }
+
               $newentity = $this->Cos->People->ExternalIdentities->$model->newEntity(
                 $arecord,
-                ['associated' => ['Addresses', 'AdHocAttributes', 'TelephoneNumbers']]
+                ['associated' => $associated]
               );
 
               $this->Cos->People->ExternalIdentities->$model->saveOrFail(
                 $newentity,
-                ['associated' => ['Addresses', 'AdHocAttributes', 'TelephoneNumbers']]
+                ['associated' => $associated]
               );
 
               $this->llog('trace', "Added $model " . $newentity->id . " for External Identity " . $externalIdentityEntity->id);