Wednesday, January 11, 2023

iCloud Drive Contingency

Mere Civilian:

iCloud Drive has been my files sync solution for over 3 years now. Before that, I was using Dropbox and never had any issues with sync. Dropbox “just works”. Unfortunately, iCloud Drive does not. Randomly, files will not sync or take too long to sync. At least on two occasions, entire folders disappeared as well. It works most of the time though and since I am all in the Apple ecosystem, it is the most simple and straightforward.

In addition to sync issues (which admittedly are few and far between), there is no way to ensure files remain offline in any particular device. This is largely an issue on iOS devices because, on the Mac, files appear to be available offline whenever I have needed them.


I am going to use Microsoft’s One Drive as a backup solution, thanks to the simple but effective SyncTime Mac app.

I’m using iCloud Drive these days for files that I want available on my iOS devices, but it’s really annoying that I can’t mark them as always available offline. Even after manually downloading files in the Files app, iOS will decide to evict them within a matter of days, despite 100 GB of free space on my phone. Just when I’m away from cell service and want to access a PDF map that I had downloaded, it’s gone.

Fingers crossed, but syncing has been reliable lately in my limited use.


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iCould has also other problems. Even when iCloud was never ever used, if you uncheck iCloud Drive in "Apple - System Preferences - Apple ID - iCloud" (to prevent the annoying "This Mac can't connect to iCloud because of a problem with" after Mac booting), then the local Mac contents of "Apple Mail - Preferences - Rules" and "- Signatures" are automatically wiped out without warning. Really frustrating! Using Appel Mail 16.0 (3696. on macOS 12.6.2 (21G320) Monterey on Intel Mac.

@Mex That’s related to what I wrote about earlier this month. The iCloud Drive settings also turn off CloudKit and other stuff that’s not really part of iCloud Drive.

This is no defence for iCloud (I'm have the same issues as Michael describes) but Dropbox was not without its issues for me either. My (former) Dropbox folder is littered with duplicate or semi duplicate files and folders structures with "(Unicode Encoding Conflict)" appended to the file/folder names. This is a known issue that's been going on for years for people with other languages as their operating system (like Swedish in my case).

As a workaround you may want to copy such files to “On my iPhone” section in Files. Annoying? Probably but at least there’s zero chance of them being evicted from the device.

@winmaciek Yeah, that is probably a good idea. It’s rather awkward. The Copy command doesn’t seem to let me copy it (no folder chooser, no way to paste). So I used Duplicate and then Move. Move actually copied rather than moving. And then I had to Rename to remove the number that Duplicate had added. Or maybe Move always copies if you pick a different storage location? I’m not sure I want to rely on that because there doesn’t seem to be any Undo.

Microsoft One Drive has an annoying limitation: It doesn't let you use chacters in file names that aren't allowed on Windows. So, if you use quotes, backslashes, asterisk, question mark and some others, you can't sync them. OD will report the issues, but if it's a folder that's misnamed, the msgs can be quite misleading.

Dropbox no longer "just works" either, ever since moving to fileproviderd.

I switched to and have had zero issues.

Don't use's beta app because Sync will stop working between macOS and Windows.

@mjtsai Huh, copy worked just fine for me just now. I went into iCloud Drive, tapped and held on a file and selected copy. Next, I went to On my iPhone, tapped and held on empty space and there was an option to paste it just fine.
Regarding, the move option, I have noticed that the moment you select On my iPhone as a location, the button in the upper right corner changes from “Move” to “Copy”. Also, dragging a file from iCloud Drive and dropping it onto On my iPhone also makes a copy. So this bit seems to be working as expected. Maybe it’s an attempt at replicating Finder’s behavior (drag and drop behavior can change depending on whether the “physical” location of a file changes?
Lack of undo, even the “shake to undo” one, is shockingly bad and somewhat atrocious even.

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