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Your friend will hopefully be lucky.
The EU is planning to replace the current system of manually stamping passports with a fully automatic EES (Entry-Exit System) based on passport scanning, but this has yet to be implemented. It was scheduled for 2022, then repeatedly pushed back. The latest launch date was to be five days ago (10 November), but last month the European Commission announced it was being postponed again.
So at the moment, any checking of the 90/180 rule can only be done by examining passport stamps and most border police don't have the time to do this.
However... if the border police detect the overstay your friend can be fined and the amount of the fine varies tremendously from one country to another (Italy is a maximum of €10,000). So I would suggest he/she checks the fine range for the various countries on the Internet, and exits from the cheapest!
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"For sheer delight there is nothing like altitude; it gives one the thrill of adventure
and enlarges the world in which you live," Irving Mather (1892-1966)
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