diff --git a/native/backup/backup-handler-context-provider.js b/native/backup/backup-handler-context-provider.js
--- a/native/backup/backup-handler-context-provider.js
+++ b/native/backup/backup-handler-context-provider.js
@@ -251,7 +251,12 @@
       step = 'computing conditions';
       const shouldDoMigration =
         usingRestoreFlow && !currentDeviceList.curPrimarySignature;
-      const shouldUploadUserKeys = isPrimary && !latestBackupInfo;
+
+      const userKeyUploadFailed =
+        restoreBackupState.status === 'user_keys_backup_failed' ||
+        restoreBackupState.status === 'user_keys_backup_started';
+      const shouldUploadUserKeys =
+        isPrimary && (!latestBackupInfo || userKeyUploadFailed);
 
       // App has UserKeys backup, but without UserData, and this is the first
       // ever compaction upload (after restore or registration).