I'm currently a Jamaican national studying in Italy since September of last year. My student visa is valid till the 4th of September this year and my Permesso di soggiorno (residence permit) expires on August 31st. My institution bought tickets for my return flight on the 1st of September where I'll transit from Venice to Frankfurt to Jamaica in the same day. They informed me today that there's a problem since my return ticket is for the day after my permit expires, however, I've left the Schengen area already this year and never have they once asked to see my permit. Will I have any problems leaving Europe without an expired permit and valid student visa?
From this Travel SE question:
The IATA statement reflects a Directive of the Italian Government's Interior Ministry which allows one to leave and return to Italy with an expired Permesso di Soggiorno, as long as one has the “ricevuta.”
You are allowed to exit Italy with it expired. You will be fine.