I am not too sure about this. Best to ask your school's DSO in these student matters, for they are the ones who know best, simply because they encounter such situations day in and day out.. We don't.
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Your grace period starts upon expiration of your F1 status and ends in 60 days regardless of the quality and quantity of applications you file with USCIS, unless one of those is approved and changes the equation. If you are not sure when your F1 status ended, talk to your DSO.
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Talk to your DSO, it appears that your grace period expired in June.
They may be able to help you reinstate.
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