Can i enter italy again? US student

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HAD i known this, i would have applied for a schengen visa in june

A (type C) Schengen visa cannot help you. The limitation of no more than 90 days in any 180-day period applies to people who hold type C visas just as it does to those (including you, as a US citizen) who can enter the Schengen area without a visa. If you apply for a Schengen visa for a trip that would exceed the 90/180 limit, the visa is supposed to be refused.

You can be authorized to stay longer than 90 days in a 180-day period by either a residence permit or a (type D) national visa. The two are essentially equivalent in that regard. I presume that you entered Italy with a long-stay visa but that "i was unable to do the whole permit thing" means that you never applied for (nor received) a residence permit.

Your question does not state when your long-stay visa expired, but if you remained in Italy more than 90 days after it expired then you were certainly present without authorization. It's also possible that Italy would regard you as having been present without authorization from the day after the permit's expiration: some Schengen countries maintain that a visa-free stay must be triggered by leaving and re-entering the Schengen area. I do not know Italy's position on this question.

If you were present in Italy without authorization, then you are presumably subject to a fine and/or a ban, or perhaps some other punishment, but you are correct that they would normally have imposed this when you left. That's no guarantee that they won't figure it out at some point in the future.

If you have been outside the Schengen area for more than 90 days, then your 90/180 "account" is sufficiently clear that you can enter for a new visit of up to 90 days. However, it's still possible that they might have you in some database because of some earlier unauthorized presence.

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