I’ve tried to pull it off on two Ryanair flights recently and the answer is: yes, they allow it. No one bothered to check the dimensions of my laptop case, but they did ask to measure the large bag on both occasions.
On the last flight the cabin was so full, some people were forced to surrender their hand luggage to be checked into the cargo hold, but my laptop bag was still safely ignored. I can’t guarantee an overzealous employee somewhere won’t bother checking the exact dimensions of the second bag, but it seems quite unlikely.
From experience, if it doesn’t fit WITHIN their measuring boxes, they won’t allow it. This means that if it doesn’t fit with/depth, or if it sticks out the top (as you’re saying with the laptop), they’ll deem it too large.
If your case is soft and can be folded up, I’d suggest considering having the case in your pocket, so that the laptop still fits in the measuring box, and then putting it back in the case once on the plane. However, there are risks with this (damage to laptop, or them still not buying it – asking where the case is?).
It’s a budget airline. They have strict rules, and charge less. Unfortunately sometimes this means the rules cause us difficulties, but it’s the choice we make when flying with them.
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