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If someone has a Schengen visa from Croatia and leaves the Schengen area in time by travelling to Serbia for example, will the authorities know, that the individual left the Schengen area in time? How is overstaying analyzed? What if on exiting Schengen you do not receive a stamp for some reason? Would this indidcate that this border crossing may have not properly recorded your exit and you run the risk of receiving a Schengen penalty? Should you keep proof of exiting the Schengen area (for example boarding passes or other documents), just in case you receive such a penalty? I guess there is no way of notifying someone who received such a penalty, so you will not know until you try to apply for a Schengen visa again?

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How is overstaying analyzed?

By examining passport stamps. Once the Electronic Entry-Exit System comes into use, the records in its database will be used instead.

What if on exiting Schengen you do not receive a stamp for some reason?

Then you can use alternative evidence to show your movements. If the Croatian border guards give your passport back to you without having stamped it, you can (should) ask them to stamp it.

Should you keep proof of exiting the Schengen area (for example boarding passes or other documents), just in case you receive such a penalty?

It can't hurt, but if you have a passport stamp then it will only be useful if you lose your passport.

I guess there is no way of notifying someone who received such a penalty, so you will not know until you try to apply for a Schengen visa again?

You gave them your address in the visa application. If you haven't moved, they can reach you there. But normally they would penalize you when you leave. So once you're out, you're not going to get a penalty. The consequence of failing to have your passport stamped is that a border officer or consular officer evaluating future application for entry or for a visa might think that you had exceeded the 90/180 limit.

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    IME from doing translation at the border: At least in Germany you'll be told about being charged with overstaying as you're leaving, and you'll be asked for your address.
    – ave
    Commented Nov 17 at 12:16

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