I used this as my "personal item" to carry on flights for a 2.5 week trip around India. It does slip over the handle of my roller bag, but gets caught and is difficult to remove when there is stuff in the bag which was an annoyance every time I boarded or needed to load bags into a vehicle/hotel room. My 2016 iPad Air with a keyboard case (so about double thickness) barely fit in the padded pocket, a larger iPad would not. My biggest issue is that one end near the zipper has already started coming apart. I did stuff it pretty full at times, and it's pretty cheap so I guess you get what you pay for. It's definitely something I would expect to hold up better in a quality bag, though. If you pack light or aren't worried about longer-term durability, it's not a bad bag.
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