By design. The automatic close only touches delivery dates that have never been auto-closed. Once the job has closed a date and you reopen it from the dashboard, the date keeps its original auto-close timestamp and is skipped on every later run — otherwise the job would immediately undo your reopen. The dashboard warns you with "The system closed this day automatically on … and you reopened it. You will need to manually close this day." The storefront also honours your reopen: customers can select meals again for that date even though the cut-off time has passed. Remember to click Close Meal Selections yourself when you are ready.