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Layover time at JFK

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I am about to book a flight with American Airlines (SF-JFK JFK-Milan) The flight going to Milan has a layover time of 2hrs and 45 minutes, but the return flight only has 1hr and 50 minutes between flights. Both planes arrive and depart from T8. Will that give me enough time to do everything I need to do (I am a naturalized American citizen) Also, I'd like to know if I have to leave the terminal to go through customs. Do I have to take my bags to the AA counter myself after customs? The last time I flew with Delta and, if I recall correctly, there was an area behind customs where we left our bags (or maybe it was just wishful thinking!) Thank you in advance.

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