I found a very simple solution on (https://apple.stackexchange.com/questions/264915/icloud-drive-is-stuck-uploading-items-and-no-longer-syncs) - opposite no 16 in red on the left of the answers: Open Terminal and type in killall bird and it worked in a flash. Whether it has any other consequences, I have no idea!
In Finder, if I just duplicated the stuck file it would make a copy and then the original would immediately sync too.
For me this was a .md file, so I can't vouch that it will fix other files with this problem. But duplicating it seemed to jump start the sync, and then I deleted the copy and that synced right away too. Hope that helps someone. That's under Monterey 12.3.
I am having the same issue with my Mac and now all of the folders and docs have disappeared off my desktop. Any answers to this issue?
Move files off desktop (or off of/out of iCloud area) waiting to upload then replace.
My Scenario: File folder located on Desktop stuck in 'waiting to upload' status is moved to removable drive. Delete folder waiting to upload off Desktop. Them move folder back from removable drive to Desktop. Folder then uploaded. That has solved my issue for the moment. Hope it helps.
i found that renaming the folder restarted the sync process. if you have a lot of folders in the state "Waiting to Upload" then this simple technique may not be suitable. In my case i had two desktop folders, one very small and the other quite large(~4GB) but the rename process worked for both of them
Was having waiting to upload issues, and logging in Issues. tried a number of the solution suggested nothing worked. I eventually found a the solution .I had Radio silence App running in the background . It was blocking network communication with icloud. I removed the the app. All issues have been resolved
I have had this issue twice. The first time was resolved when I updated my Monterey operating system. Recently it happened again. I believe I know what caused it, at least in my instance. I created a file in the FILES app on my phone and immediately deleted it. I don't think it had a chance to upload to iCloud and when I check the folders on my M1 Air, Waiting to Upload appeared.
This time I shut off Desktop and Documents on both Apple devices that I had syncing (M1 Air and iPhone). I deleted the Documents folder as that was the one hung up. I reloaded the documents from a backup that I had created prior. Once everything syncs all was well again. It was a pain and I only have about 15GB of documents. Hopefully Apple will get this worked out. I'm not holding my breath as many of these posts go back years. In the meantime, I'm going to give everything plenty of time to sync before I delete files.
This seems like an absurd solution, but it definitely worked for me. I had a number of apps open for quite a while, so I closed all of them, and the small file that had been hung up for days uploaded instantly. I'm on an iMac with an M1 chip. Try it, it's an easy solution if it works and no sweat if it doesn't.
Having the same problem but besides the solution mentioned here, but cabled internet works also. Much easier. Do not know if it works for everyone though
I logout of the Mac and login immediately , the files upload right away. But this seems to defeat the whole purpose of icloud. I use dropbox in the past and never has this problem!
A simple killall bird command in the terminal works perfectly for me.
It is probably related to the synchronization process priority, which got so low in priority that stuck in the progress.
When you kill the process the system automatically restart it and finish the sync correctly.
A perhaps similar or related bug was reported via Apple Support, it's discussed on Apple Community here:
TLDR: Try disabling time machine back ups.
After dealing with this problem for a very long time, I had given up on it. iCloud just always seemed to get stuck. I decided to try to fix it by doing a clean reinstall of the OS (Monterey). But that didn't fix it.
Finally, I noticed that the syncing with iCloud Drive did was blocked by a time machine backup process to an external hard drive. Once I disabled time machine (and ejected external hard drive for good measure), the sync started working perfectly.
I have already tried several solutions. The only thing that works to me is to create a new folder, transfer the contents from the old folder to this new one and repeat this process for all the folders above the one that presented the problem. This problem is extremely annoying. I have found reports of this bug in several foruns, but none with a definitive solution. I've tried Apple support and they couldn't find the solution.
I also experience a similar issue (macOs Monterey) when I turn off icloud drive and turn it on again the icloud drive folder keeps loading saying (intalling Icloud Drive) while nothing happens. I cant reach my folders. This doesn't solve after restarting my device. Also, when I want to turn on the yncing between desktop and documents in icloud preferences it doesnt do anything. A frequently occuring issue but can't seem to solve both.
Were you able to fix the problem? I was having the same issue. I think I found the solution though. You know how we uncheck the background and documents backup in the iCloud settings? After I checked that, it started uploading again and I was able to use in other apple devices. Try if that works...
Same problem.
In my case, I discovered there were some hidden files. After getting rid of them, everything went back to normal.
In fact, it started as a suspicion, because all the "regular" files were uploaded, so I suspected that something else should be interfering with iCloud.
I prefer to use the Terminal in such cases, so I 'cd' to the folder and there they were: two temporary hidden files left by MS Excel. I couldn't delete them using the regular "rm" command, thus I decided to go around it - I copied the files that mattered to a temporary folder, removed the folder that won't upload to iCloud (with all the hidden file on it) and then recreated it and moved the files back.
Now my folder's sync'ed and no more "Waiting to Upload".
Guys, I may have found a solution. I had the same problem Desktop and Documents didn’t sync and stuck on Waiting to Upload. I uploaded only one file through icloud.com to see what would happen and it somehow fixed everything. The files appeared on my iPhone and everything. Try it out yousrelves.
Has there been a solution for this yet? I am having this issue with one of my staff machines. I was able to copy one of the folders to her desktop, but iCloud is still "waiting to upload her remaining 2 folders" and she can only access her files through iCloud online. This started to occur 2 months ago when she upgraded to Monterey.
Very strange behavior. This happened to me from times to times. Right now, it was same but at almost the end of upload (="uploading" vs "Waiting to upload"). I tried to cancel the copy but could not. No effect on the cross. I went to Force quit to close the finder from there : Finder icon had wrong icon, from another app. I closed that app. File copy finished without doing further command.
Just like if there were some process mix. The files I tried to copy were not related to that app.
Quite strange! This problem is here for some years and no clear answer.
I am also having this problem.. I've had it on Monterey & now Ventura. I have not been able to find a solution. Restoring, Restarting Bird, Signing in and out do not resolve the problem.
I had hopes that with Ventura the problem would be solved, but it seems not. Maybe it's time to look for another app for syncing files. Too bad Apple!
Just ran into this problem again, read this thread, and felt given the wild postulated solutions here, that perhaps Occum's razor likely applies. While I have not extensively tested the hypothesis I'm about to present, given the relative simplicity of actions I took to address the issue, I feel strongly that my thesis is close to the mark.
Multi-device sync is a non-trivial exercise; there are numerous non-deterministic actions that can occur on either side of a sync session that can cause one side to "time out" or otherwise drop/pause/hang the connection and thus "hang" the process of synchronizing, leaving the other side "waiting by the sea". In my case, I had a folder with a word document and some PDFs all stuck with the "sync cloud" displayed and "waiting for upload" on the parent folder. This seemed like the classic "hang", perhaps initially caused by MS word writing to the file at the wrong instant, causing a lock contention, and thus hanging the process, and the mac waiting patiently for iCloud to re-engage, which it was never going to do.
My fix? I opened the word file, added a space character, and saved the file (yes, yes, I could have used "terminal" to "touch" the file, but this was easier). This "change" caused macOS to "restart" the sync effort, and iCloud responded, and the upload of all files was immediate and complete. Ideally, MacOS should set a state flag and sync_in_progress_duration for itself, and "time out / restart" sync efforts that have been placed in "pause" for an excessive amount of time should have the whole sync process restart. Again, not necessarily simple to fix, but my guess is there is more that can be done ala TCP/IP-like backoff and retry that would mitigate most of these hangs.
So, the thesis is "sync is hard; touching files, while annoying, is easy. Make a change, save your sync."
Hope that helps.
