I've tried to pull it off on two Ryanair flights recently and the answer is: yes, the 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 might bother checking the exact dimensions of the second bag, but it seems quite unlikely.

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.