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I know this American guy living out of Hostels in Krakow, he has no fixed address, no work visa (but is working illegally) is more than 1 month outside his 90 and out (infact on and off he has been in Poland for about 2 years)!
Good luck to him.
If he goes to Ukraine, is he likely to be banned from re-entering Shengen area or are they likely to just let him back in anyway?
If he goes there, he's got a high chance of being picked up (they scrutinise all documents very carefully on the Eastern border, even EU documents) and banned from re-entry.
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