Can't delete failed Airdrop items

I use Airdrop a lot, usually without problems. Today it keeps failing and I now have about 250 0Kb items which give me the following message when I try to move or delete them.

"Some of the items you are moving are in use by another application. Moving the items can cause problems with the application using them. Are you sure you want to move these items?"

No clues as to which application might be trying to use them, unless it's Preview. And yes, I have restarted both my phone (sender) and my MacBook (twice). They appear to be taking up about 1.5GB of space in spite of not having any content.


MacBook Pro 16″, macOS 14.1

Posted on Jan 23, 2024 10:52 PM

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Posted on May 23, 2024 12:09 PM

I ran into this problem today, and here's how I solved it: I used an app called "Find Any File" to search for those problem files in my Downloads folder. Within this app, I right-clicked on the problem files and chose the "Move to Trash" option, which worked. I could then empty the Trash the usual way.

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Question marked as Top-ranking reply

May 23, 2024 12:09 PM in response to janiemt

I ran into this problem today, and here's how I solved it: I used an app called "Find Any File" to search for those problem files in my Downloads folder. Within this app, I right-clicked on the problem files and chose the "Move to Trash" option, which worked. I could then empty the Trash the usual way.

Jan 24, 2024 10:20 PM in response to janiemt

> I tried on the 'Disk image' got a message to say the computer would be unresponsive


Which disk image?? You don't usually/ever have to check the Recovery etc disk images that the Disk Utility might show.


> They're 'loose' in my Downloads folder


You could move (or delete) the other files in the Downloads folder elsewhere so the next steps might be easier. How many and what kind (suffix) files the stubborn files are (10?, 1000?)?


You could reboot into recovery mode and launch the Terminal there (so no app should hold on the stubborn files). Then move to the ~Downloads folder (use something like cd '/Volumes' (use those quotes to escape possible spaces in the folder names) then check what folders are there with 'ls', then proceed one folder at a time to something like cd /Volumes/'HD - Data'[my internal disk name is HD, YMMV]/Users/[me]/Downloads').


Then in the Downloads folder 'ls' to check its contents and try to remove the 1st file with (again use quotes to escape possible spaces in the filename), confirm delete with 'y' or cancel with 'n':


rm -i 'stubborn file.jpeg'


If that does not succeed, try (it prompts for your Mac's admin password):


sudo rm -i 'stubborn file.jpeg'


If either one works (and the file vanishes), delete all stubborn .jpeg files in that folder (make sure you are still at the Downloads folder with 'pwd' command) with:


rm -i *.jpeg


Leave off the confirming option '-i' if you are confident everything is going OK and there are numerous such files. Then check with 'ls' if there are other files with other suffixes that must still be deleted.


https://www.howtogeek.com/858815/linux-rm-command/


There was a similar thread recently. It might be an option to try to delete some preference file etc but maybe someone else will chime in about that. If uncertain, you can ask some unix person for help or consult some Apple authorized dealer.


I accidentally dropped 86000 pics onto th… - Apple Community


Optionally, you could try to re-install Sonoma 14.3 on top of the old install (as always, do a backup first although the user data is left intact).


If all else fails, you could backup, reformat and restore.


Jan 25, 2024 12:35 PM in response to Matti Haveri

Hi Matti

Thanks so much for all the time and effort you're putting into this.


It seems to me there are two things going on here. Apart from these rogue files, Airdrop has become erratic - works sometimes but more often 'Fails'. I looked this up as well and it seems to be a common problem since the introduction of Sanoma and has persisted through 3 updates. These first of these files were left after one of these failed Airdrops. I tried again a couple of times with just a few and it kept happening. I have since had limited success with Airdrop. Such a pest because a project I'm doing involves transferring a lot of photos on a regular basis. I'll write to Apple and push for a fix. (Someone in the Sanoma/Airdrop thread was urging everyone to do that).


> I tried on the 'Disk image' got a message to say the computer would be unresponsive

>> Which disk image?? You don't usually/ever have to check the Recovery etc disk images that the Disk Utility might show.


Reply: Sorry - I might have got the name wrong, would have to go back into Rec mode to check this - it was the second volume available to run DFA on - showed up my SSD card and also this, both had containers.


> They're 'loose' in my Downloads folder

>>You could move (or delete) the other files in the Downloads folder elsewhere so the next steps might be easier. How many and what kind (suffix) files the stubborn files are (10?, 1000?)?


Reply: There are 149 and they are .heif/HEIF image files. and yes, I have removed everything else. After doing the DFA, I managed to Airdrop the rest of that lot of photos in small batches and removed them from Downloads each time. I had a couple of fails but didn't get any more of the rogue files so it might have fixed something even tho I still can't delete them.


I'm a bit nervous of the terminal - I have used it but only on an old Mac where I had nothing to lose. It seems very easy to do a lot of damage with the wrong command.


I'll print out your description and try it when I have a clearer head and more time than I have at this moment. The I can cross it off as I go and be really sure I'm following carefully!


And yes, I do have two backups on separate Time Machine externals, but I also wonder if reinstalling from Time Machine wouldn't just reimport all the old problems. Last time I reinstalled a fresh system and just copied the apps and data from the backups.


It's still under AppleCare - I've been considering taking it to our dealer, but I get worried about letting other people mess with it!! They didn't impress me hugely in there when I bought it!


Thanks again so much for all your help. I'll let you know if I get brave enough to try the terminal!

Cheers, Jane




You could reboot into recovery mode and launch the Terminal there (so no app should hold on the stubborn files). Then move to the ~Downloads folder (use something like cd '/Volumes' (use those quotes to escape possible spaces in the folder names) then check what folders are there with 'ls', then proceed one folder at a time to something like cd /Volumes/'HD - Data'[my internal disk name is HD, YMMV]/Users/[me]/Downloads').


Then in the Downloads folder 'ls' to check its contents and try to remove the 1st file with (again use quotes to escape possible spaces in the filename), confirm delete with 'y' or cancel with 'n':


rm -i 'stubborn file.jpeg'


If that does not succeed, try (it prompts for your Mac's admin password):


sudo rm -i 'stubborn file.jpeg'


If either one works (and the file vanishes), delete all stubborn .jpeg files in that folder (make sure you are still at the Downloads folder with 'pwd' command) with:


rm -i *.jpeg


Leave off the confirming option '-i' if you are confident everything is going OK and there are numerous such files. Then check with 'ls' if there are other files with other suffixes that must still be deleted.


https://www.howtogeek.com/858815/linux-rm-command/


There was a similar thread recently. It might be an option to try to delete some preference file etc but maybe someone else will chime in about that. If uncertain, you can ask some unix person for help or consult some Apple authorized dealer.


I accidentally dropped 86000 pics onto th… - Apple Community


Optionally, you could try to re-install Sonoma 14.3 on top of the old install (as always, do a backup first although the user data is left intact).


If all else fails, you could backup, reformat and restore.

Jun 11, 2024 4:05 PM in response to JayaII

Lol that app worked for me. First I made a new folder and called it TRASH, then I put all the failed airdrop files in the folder(Clicked Continue for all the Warnings about moving the files), then I opened the app "Find Any File", typed in TRASH, then found the folder and selected it, right clicked it, then clicked "move to trash". Then finally just empty the trash like normal on Mac. This is a big L for Apple I expect them to resolve this quickly cause we cant be the only ones running into this problem.

Jan 24, 2024 1:04 PM in response to Matti Haveri

Hi Matti

I tried deleting the items in Safe mode and unfortunately got the same message. (They're 'loose' in my Downloads folder and I get the same message if I try to move them into a new folder, so they're really making a mess of Downloads and obviously I can't delete that folder!)

I then started in Recovery mode and ran Disk First Aid which told me everything was OK on my SSD storage (there were some warnings in the details which looked like some items (prob all the dud Download items) had lost their path, but finished up saying it appeared to be OK.

But when I tried on the 'Disk image' got a message to say the computer would be unresponsive, possibly for several hours and to run it in Recovery mode to avoid this (same message both in Safe mode and Recovery mode!)

So not sure where to now

I've been using the Photos App a lot lately and it has been crashing quite often; the empty Airdropped items I was transferring were all photos too. I wonder if I should reinstall Photos? Altho not sure if I can do this without reinstalling the System. My system is completely up to date. (Sanoma 14.3)

Thank you for your help with this - really appreciate it

Somewhere I read a suggestion to clear the Airdrop cache, but the suggested Library has a red minus on it and wouldn't allow me access



Jan 26, 2024 2:26 AM in response to janiemt

> if reinstalling from Time Machine wouldn't just reimport all the old problems


Yes that can happen so the advice is not to import old potentially corrupt user settings.


I use Carbon Copy Cloner for my backups so I don't know how granular Time Machine restore might be (AFAIK it is almost all or nothing?).


On the other hand, a Time Machine restore might ignore those rogue files by default anyway?


FWIW I usually restore everything manually from the backups but that requires some planning and a non-messy filing system so you know where the important files are. And to remember to restore items like the Mail folder and some app data from ~/Library. And to have application license numbers archived.


> It's still under AppleCare - I've been considering taking it to our dealer, but I get worried about letting other people mess with it


I wouldn't worry about that with good backups.

Jan 28, 2024 2:46 PM in response to Matti Haveri

Hi Matti

Things seem to be going ok at the moment, apart from the rogue files still being there. Airdrop has even mostly been working, altho I haven't had much time on the computer the last couple of days and haven't done any of the terminal work. So maybe DFA did something useful. I've copied all your suggestions and will try them when I get some clear time and headspace, but not right now. Thanks very much again. Cheers

May 23, 2024 6:00 PM in response to JayaII

Thanks Jayall, Just read about FAF and sounds fantastic - and useful as well - I've certainly experienced the same short comings and frustrations many reviewers are finding with Apple's built in search facilities. I'm always a bit wary of third party apps but this one gets rave reviews and seems very reliable and effective.


Can we push Apple to up their game?

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Can't delete failed Airdrop items

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