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I want to buy a PRG-MXP-TFS route on Ryanair. Obviously they don't sell tickets with connections, so those are going to be separate tickets.

When checking in at Prague airport, is it possible to receive a Ryanair passport check for both legs (I need one since I'm not an EU citizen)? Or would I have to leave the secure area at Milan airport and get another passport stamp from Ryanair's desk?

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No, officially it is not possible to receive a passport check stamp for both flights.

Source: I tweeted Ryanair if you could get the passport check stamp for both flights if one had two flights the same day and they were fast to respond that no, unfortunately not.

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That being said, I would for sure try and ask at your first departure if they would kindly also stamp your second boarding pass. I do not see anything airport- / flight-specific about the stamp as far as I can tell from the picture you uploaded to the linked post.

UPDATE:
Last time I checked luggage with Ryanair there was no queue so I asked: you do need the stamp to board - however sometimes the gate agents bring the stamp with them to the gate. If you are desperate to fly such a connection you might want to try and then contact gate agents proactively airside, ideally before boarding starts.

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    Perhaps with a bit of sleight of hand you could get them to stamp the second BP first then realise it's the wrong one – Berwyn Jul 5 '16 at 18:03
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    Shame as this makes connecting flights just a bit harder – JonathanReez Supports Monica Jul 5 '16 at 19:01

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