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Your phone sees the Mac in the AirDrop sheet, you tap its name, it says "Waiting…" — and nothing ever happens. It's one of the most frustrating AirDrop failures, because discovery clearly works, which makes it look like the problem must be somewhere else. Here are the usual suspects, plus two causes almost nobody checks.
Wi-Fi AND Bluetooth turned on on both devices — AirDrop needs both to set up its direct link, even though no data actually goes through your router.
Receiving set to "Everyone" (or "Everyone for 10 Minutes") on the receiving device, if the sender isn't in your contacts.
An active Focus / Do Not Disturb mode can silently swallow the incoming request banner.
Personal Hotspot turned on on the iPhone, which can interfere with the direct Wi-Fi link AirDrop relies on.
1. A second user session left open in the background — with Fast User Switching, macOS keeps inactive sessions alive. Each one runs its own AirDrop service, and they fight over the same Bluetooth channel. The request does arrive, but the accept prompt renders on the OTHER session's (invisible) screen, never on yours. Fix: fully log out — not just switch away from — any unused session before using AirDrop.
2. A Finder window with the AirDrop pane open — macOS hands off the request-approval prompt to that window instead of showing the normal system banner. If the window isn't frontmost, the request silently expires after a few seconds. Fix: close any Finder window showing AirDrop before receiving a file.
Toggle Wi-Fi and Bluetooth off and back on on both devices.
Set receiving to "Everyone".
Turn off any active Focus.
Fully log out of any other open user session on the Mac.
Close any Finder window showing AirDrop.
Retry the transfer.
One of these six almost always fixes it.