Can't send files with AirDrop since Monterey

[Ghost-Hardware]

Hey,

So I have 3 Macs all updated to macOS Monterey :

• Mac mini M1
• MacBook Pro M1
• MacBook Air Intel 2020

I've noticed an issue since I've updated to Monterey : I just can't send files from my Macs at all with AirDrop.

This is what I observed :

• I can't send files from my Macs to both macOS and iOS devices
• I can see other AirDrop devices from these Macs : both iOS and macOS ones
• I can see my Macs from the other AirDrop devices, both macOS and iOS
• I can send files from my iPhone 11 Pro (iOS 15) to my Macs without any problem
• Sometimes, when I try to send a file from a Mac to another Mac, it seems to be waiting for the receiving Mac to accept the transfer but I can't see any message to do so. On the sending Mac, when I click on the icon of the receiving Mac in the Finder's AirDrop menu, a bubble appears and says : "Waiting for <unknown> to accept" (my macOS version is in french so the message might differ a bit from the english version). The "<unknown>" looks very odd to me. And then, the transfer just fails with the appropriate message showing up.
• Most of the time, when I drag and drop a file on the receiving device, it does nothing. The icon of the device is reacting to my drop but nothing happens afterwards.
• When I try to send a file from my iPhone to my Macs, I can see the iPhone icon on the Mac’s AirDrop menu. However, when the file is transferring, the iPhone icon duplicates itself when it’s sending. Then, when the transfer is done, the duplicate icon disappears.

This is what I tried to do to fix the issue (but in vain) :

• Disconnect from my VPN on both devices
• Log out from iCloud an log on again on both devices
• Turn off and on Bluetooth on both devices
• Restart devices
• AirDrop a file with the macOS share menu

Bluetooth is on on both and they are connected to the same Wi-Fi network.

Any help?

Thanks !

 

[Jochheim]

Sadly there are a lot of broken things in Monterey. At least airdrop works for me (iPhone to Mac mini m1). I will try sending something from my Mac to the iPhone.

 

[Ghost-Hardware]

Sadly there are a lot of broken things in Monterey. At least airdrop works for me (iPhone to Mac mini m1). I will try sending something from my Mac to the iPhone.

Thanks man. I would appreciate your return about this.

 

[Jochheim]

Sure, no problem. Just tested several variants: Everything worked flawlessly (sending real files, websites, copying text) from MacBook (intel 2020) and also from Mac mini m1 to the iPhone and between the macs. The only strange thing: Between the macs the names were missing (just my user name, not the name of the machine visible). Some suggest logging out of iCloud and back in (but I am hesitant of doing this, because sometimes it creates other problems for me).

 

[Ghost-Hardware]

The only strange thing: Between the macs the names were missing (just my user name, not the name of the machine visible).

Yeah I noticed that too. You should see the name of your Apple ID and under it, the device type. But I definitely can’t see device types anymore.

 

[lookitupkid]

I'm having the same issue. I can airdrop from my iOS devices to my M1Mac, but not vice versa. The Mac sees the devices, but when I drop a file onto the device in the AirDrop box, nothing happens. All devices are completely updated.

 

[Ghost-Hardware]

I'm having the same issue. I can airdrop from my iOS devices to my M1Mac, but not vice versa. The Mac sees the devices, but when I drop a file onto the device in the AirDrop box, nothing happens. All devices are completely updated.

Thanks, I feel a bit reassured now. I was starting to think that I was alone with my 3 different Macs ... 😶‍🌫️

 

[donvito4ever]

Hi!

In my case, I send photos from the iPhone to the MacPro 5.1 and seems like is working, iPhone tell that is Ok, in the Mac the icon of Downloads jump but... no photos!!

What can I do??

 

[bolandross]

Same here, since I installed Monterey on my iMac Pro, I can't send files to my MacBook (Big Sur). Did you find a solution for this?

 

[lookitupkid]

Interesting update: I mentioned a few posts up that I was having this problem. I pulled an M1iMac out of the closet that I hadn't been using. When I updated it to Monterey, the airdrop DID work...to my dismay. Today (about a week later) it stopped working. So now airdrop doesn't work on either my M1Macbook or M1iMac. 🤷🏻‍♂️

 

[businessnumbersmoneypeopl]

Same problem here for a while now. I thought it's M1 related but so it's about Monterey, huh.

I've come across one annoying workaround. Instead of initiating the Airdrop with a right-click on a file name, you have to open a separate Airdrop finder window. By dragging the file there it works.

 

[bolandross]

Same problem here for a while now. I thought it's M1 related but so it's about Monterey, huh.

I've come across one annoying workaround. Instead of initiating the Airdrop with a right-click on a file name, you have to open a separate Airdrop finder window. By dragging the file there it works.

Thanks for sharing your workaround with us. Unfortunately, it doesn't work for me.

I currently have my MacBook 12" and iMac Pro updated to macOS Monterey 12.0.1 and AirDrop stopped working no matter the direction. It doesn't even work to send stuff to my iPhone anymore.

Sending from Mac is broken, receiving on my Macs, when sending from the iPhone works.

 

[businessnumbersmoneypeopl]

Thanks for sharing your workaround with us. Unfortunately, it doesn't work for me.

I currently have my MacBook 12" and iMac Pro updated to macOS Monterey 12.0.1 and AirDrop stopped working no matter the direction. It doesn't even work to send stuff to my iPhone anymore.

Sending from Mac is broken, receiving on my Macs, when sending from the iPhone works.

Wow, that really sucks. I really hope Macrumors would spot this thread and make an article of it, maybe that would catch someone's attention at the Apple HQ.

 

[loekf]

Wow, that really sucks. I really hope Macrumors would spot this thread and make an article of it, maybe that would catch someone's attention at the Apple HQ.

Among other bugs, always make me wonder do they actually use their latest OS in-house or only for doing nice demos in Keynotes ?

Same for the trackpad and mouse connectivity problems, that is a very annoying trivial and hard to miss bug I would say.

 

[businessnumbersmoneypeopl]

Among other bugs, always make me wonder do they actually use their latest OS in-house or only for doing nice demos in Keynotes ?

Same for the trackpad and mouse connectivity problems, that is a very annoying trivial and hard to miss bug I would say.

That's an excellent question. Personally, I use Preview a lot for doing markups on pdfs, and for several months, the program has occasionally started to teleport me to the second-last markup every time I make a new one. By this point I'm not even expecting them to fix it anytime soon, if ever. Of course I could switch to a different program (and maybe I will), but it shouldn't be too much to ask to create a working pdf reader in 2021.

 

[bolandross]

Yeah, there are some obvious flaws in the current macOS that wouldn't exist if the developers would try their own dog food on a daily basis. But I think that's valid for other companies, too. Seems like there is no time for testing anymore, since anything can be fixed via an online update later.

 

[lookitupkid]

Final update: Spent probably 90 minutes with an awesome senior advisor with Apple Care and got it working again. Somewhere in System Preferences, AdGuard was listed as a VPN. We had to ditch AdGuard altogether. An AdGuard update will eventually probably fix it. He said “VPN related issues” are probably at fault in most of these cases. He seemed pretty excited to have fixed it, took a ton of notes, and assured me that this would make it easier for them to help other customers.

 

[bolandross]

Final update: Spent probably 90 minutes with an awesome senior advisor with Apple Care and got it working again. Somewhere in System Preferences, AdGuard was listed as a VPN. We had to ditch AdGuard altogether. An AdGuard update will eventually probably fix it. He said “VPN related issues” are probably at fault in most of these cases. He seemed pretty excited to have fixed it, took a ton of notes, and assured me that this would make it easier for them to help other customers.

What a great guy, thanks for spending your time on the phone for us. I have only reported the bug via the feedback form, but this Apple employee response is really helpful!

I am too using AdGuard but never had these issues on Big Sur. It seems like some security surroundings for VPN connections have changed in Monterey.

Knowing this, I can quickly flip the switch to deactivate AdGuard when wanting to use AirDrop on the sending machine (until there is a better solution). Good stuff!

Have you contacted AdGuard support regarding this? If yes, do you have a ticket number I can refer to when reporting this, too?

 

[empersance]

I have some issues too on Airdrop, especially if i Airdrop stuff to myself (same account)

From iPhone to Mac mini M1 is fine, viceversa instead:

• If I'm in Finder -> Airdrop, it works without asking anything, with the sound of downloaded stuff, and the file is downloade
• If not in the finder, I don't see the notification to accept but i hear the sound of notification, but the file is not downloaded

It's very strange