Never worked for me, not even once.

I tried on three phones, two of which are using the same account, I'm reasonably confident I am technically competent to not make silly mistakes, though the best I've achieved was endless wait.

I had better success with IR and BT file transfers. Hell, even spinning a local http server (with python -m http.server) works better than quick share.

Idk what Quickshare is, but AirDrop has only worked like 25% of the time for me