AirDrop sometimes just doesn’t work and gives you zero tools to debug why. In my experience airdrop between phones seem to work fine (probably helped by UWB), but involving Macs makes it an unreliable mess. Staring at the “there is no one nearby to share with” screen with little you can do. Bonus points when it’s asymmetrical: the Mac finds the iPhone just fine but the iPhone cannot find the Mac. When the device is finally found, tapping on it does not cause the other device to present any UI whatsoever to accept the transfer, and the sending devices simply displays “Declined” after a timeout. And if your Mac has multiple user accounts (traditional UNIX-style security boundary) it is undefined which user account will receive the notification to accept the transfer.
I haven't had AirDrop fail on me, but I have had other similar issues with Apple's "ecosystem" integration.
And that's the frustrating part of using Apple. When it works, it works great. When it doesn't work, you have zero visibility into what's happening or what went wrong, and no tools to debug. It's just a magic black box and you are SOL.
