Does this bag fit into an airplane’s overhead compartment? I’m a type one diabetic and am looking for a travel bag for insulin pump supplies.

No, it will not. It is too large by only a couple of inches.

It just comes w/the bag and trolley correct? No medical supplies right?

Yes, the supplies are not included.

Does the bag stay on the trolley securely? Does it ever tip over?

Yes, it does stay on trolley. The bag is secured with 4 straps of heavy duty velcro. My son's Nurse pulls it around Highschool with Medical equipment. She said it worked well.

Did they fix the design flaw and put the flap inside so the zipper on the bottom can be closed?

Nope. The flap is still sewn outside the zipper.

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