Airdrop stopped working: grey icon with question mark

2SSophie wrote:

Thanks for your suggestions @leroydouglas,

You're right, Airdrop has always been moody...

We used to use file sharing, but Airdrop is so convenient (when it works!)

We tried absolutely everything on the links you mentioned: it didn't get better, unfortunately.

BUT, I have good news, my husband is a genius :-) He just found that the AdGuard software we are using (an add blocker) was the troublemaker!

I made a mistake on my previous post: the issue occurred when he upgraded to Monterey. To sum up: AdGuard gets mad at Airdrop on Monterey.

When AdGuard is activated on his MacBookPro, he can't see my icon on Airdrop. When he turns AdGuard off, my icon appears.

On my side (Catalina), AdGuard can be on or off, I always see my husband's icon on Airdrop.

-> Even better news: he modified his settings, now everything is working just fine.

So, if you are using AdGuard on Monterey, this is what you should do:

In AdGuard, go to : Preferences > Network > Automatically filter applications > Select mode --> check Automatic proxy instead of Network extension.

Problem solved, I hope it will help other Airdrop users!

It is always advise to

Uninstall all third party apps that are Cleaners/Optimizers/VPN/Anti-Virus

all known to cause issues on the macOS

if in doubt visit the developers website—uninstall

https://adguard.com/en/blog/adguard-2-5-for-mac.html

2SSophie wrote:

Hi Apple community!

Long time Airdrop user here: my husband and I regularly transfer documents to each other's Mac (or I should say Macs: 2 MacBookPro, 2 iMac). Airdrop used to work fine, most of the time.

It stopped working recently: I can see my husband's icon on my Airdrop window on my Mac, but he can't see my icon. More precisely, he sees a grey icon with a question mark, instead of my icon. Also he can't interact with this icon: if he tries to send a document, nothing happens, and I don't receive any notification.

I can send him documents, since I can access his icon, but he can't send me anything.

I have not seen this "question mark icon issue" on any other forum.

I'm running on Catalina, he's on Monterey. Same problem with both MacBookPro and both iMac.

AirDrop stopped working shortly before he upgraded to Monterey (he was previously on Big Sur).

We have already checked the WiFi & Bluetooth settings, multiple shut down/restart.

On both sides, "allow me to be discovered by" is set on "everyone".

Any clue? Thanks in advance for your help.

Airdrop has always been a bit finicky, sometimes it works sometimes it does not has been my experience...

Airdrop Requirements and some Troubleshooting

https://support.apple.com/en-us/HT203106

Airdrop - Using

https://support.apple.com/en-us/HT204144

AirDrop, here are some fixes

https://www.imore.com/how-to-fix-airdrop-iphone-ipad

You can use file sharing as an alternative

Set up file sharing on Mac - Apple Support