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How does Denmark know when you arrived in the country from another Schengen country?

An American friend wants to come visit me in Italy for 2 months, and then go to Denmark for 2 months. (Denmark allows 90 days in addition to previous Schengen time: https://www.nyidanmark.dk/en-us/coming_to_dk/visa/Visa_free_travel.htm)

But how will Danish authorities know when he arrived in Denmark? Will he get in trouble when flying to the U.K. 120 days after he arrived in Italy?

Helpful first-hand knowledge most appreciated. Guesses based on experiences in other countries less helpful, since Denmark is a special situation.

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Your friend have to be able to prove where he was (airtickets, boarding passes, hotel bills - showing "last day uin Italy+first day in Denmark") - and very wise to leave DK for a non-Schengen country.

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