A job inside a box runs only once per box execution even when there is a cyclic time condition defined on the job.
This is working as designed. Each job in a box will run only once per box execution.
Therefore, you should not define more than one time attribute for any job in a box because the job will only run the first time.
If you want to put a job in a box, but you also want it to run it more than once, you will need to assign multiple start time conditions to the box itself, and define no time conditions for the job.
Another possible solution is restart the box on success of the inner job.