Windows hosed my iCloud—Backups save the day!

Windows ate my iCloud files for a midnight snack last night. I have several Macs and iOS devices that I use at home and at work. I use iCloud to keep all my documents in sync. Seldom do I have any problems.

I also have a “Windoze” computer that I use at home to run a few Windows-only apps. I put a copy of iCloud on that computer mostly to help transfer files between the two and figured another copy of my iCloud files can’t hurt anything. Well, I updated Windows last night and somehow it corrupted my iCloud folder on that machine. To iCloud, it looked like all my files had been deleted.

So the iCloud service on Windows dutifully started deleting all my files from the cloud!

By the time I got to work this morning, virtually all the files in iCloud were gone. I thought it was peculiar so I remoted into my home Mac and the files were gone there, too. My final hope was that something was broken with the link to the cloud, so I logged into and all the files were gone there, too.

I opened time machine and the files ere gone there, too in the present, but when I went back to last night—before the Windows update—they were there. 7:15 pm all was good, 8:15 many of the files were gone, 9:15 everything was gone…

A quick call to Apple just to be sure I could simply restore the files to my Mac and let everything sync. They checked some secret “recently deleted files” cache that they keep on iCloud, but no files there either. So I stopped the iCloud service on Windows, uninstalled, deleted the remnant iCloud files from Windows, then restored my time machine backup to my Mac. All is well again.

How’s that for a peculiar problem? And, how’s that for verification of the importance of a solid back up routine. In addition to both my Macs running time machine backups, I use Backblaze and occasional SuperDuper clones.

Lastly, I cannot complement Apple enough for their support. Extremely prompt response, I was quickly escalated to senior support, and they helped me verify that the restore would work as expected. My sons rib me about the “Apple Tax” I gladly pay. And this is one reason why I do so…

I’m happy for you that you were able to get your files from Time Machine. But there’s a non-secret recently deleted files section you can check; iCloud is supposed to retain all deleted files for 30 days, and anyone can look at and recover. Check for yourself, maybe the files are still there!

Yes, we checked that too, and there were only two folders there that I intentionally deleted earlier in the week. Nothing else, sadly.

I’ve also had issues with recovering recently-deleted files from iCloud (within 30 day limit), so it can’t be 100% reliable.

This article from Backblaze ( comes to mind - always remember the difference between sync and backup.

Yeah, I don’t think any of us here are thinking iCloud Drive is a back up. Clearly syncing. What this experience has demonstrated to me is the importance of a strong, reliable, automated back up strategy. For years many thought my back up process is overkill, but really it’s a lifesaver. especially because these are business files. Without them, I am out of business.