iCloud Drive via (macOS) app?

I have a horrible feeling I already know the answer to this, but I will ask the hive mind in probably vain hope.

Other than using a web browser, is there any way to upload files to iCloud Drive via an app?

I’ll spare everyone my ranting on the issue but my MacBook Pro will not upload to iCloud in the usual way and I have been hanging on to a Mac mini as a workaround to this. I realised today that it is the ONLY thing the mini has been used for in months and I just want to get shot of it. I’d rather have (a working iCloud and) some money in my account for other tech gear.

Has Finder not worked for you? If not, is there indication of a failure?

Oh, I’ve done the whole 9 yards with Apple, twice, and they have acknowledged a bug which they will fix… sometime… but in the meantime, no, Finder won’t do it.

To be honest, I was sparing myself more than anyone else in not doing the full rant because it makes me so angry. I did write it up here, though.

I’ve had this problem once with a 2011 macbook air, and a nuke&pave initially solved but it reappeared later. What definitely solved it was going to a different AppleID. I changed the email address for it and logged out and back in, and I don;'t know if that fixed it for me, but I have not seen it happen since (touch wood)


I just finished reading your “full rant” and all I can say is you are not alone. I’ve had many of the same problems for years, on multiple machines, even when using symmetrical gigabit internet. iCloud seems to sync photos and contacts, etc. ok but is unreliable when it comes to files. I am baffled by this considering much/most? of iCloud runs on Amazon S3 and Google, both of which are rock solid.

So I only use iCloud when I encounter a site or service that doesn’t offer Google Drive on the Share Sheet. And frequently the file I save to iCloud will not download until I get home and drag a file into the receiving folder to jumpstart the sync.


If you can’t fix the sync issue, the only app I can think of is iCloud Drive for Windows, which you could maybe run in Parallels on the Mac. I haven’t tried it myself. Obviously that’s kind of an expensive solution; I think I’d rather keep the mini.


I recently tried iCloud for Windows on a Win10 Pro PC. It had the same file sync problems as iCloud on a Mac and I never got it to sync all my photos.

1 Like

iCloud seems to have two modes:

  1. Works Perfectly

  2. Has Severe Problems Which Cannot Be Fixed Because The System Is Completely Opaque

There seems no rhyme or reason for why someone falls into one group instead of the other, but for every person who says “Oh yeah I switched to iCloud Drive, and I’ve never had a a single problem” I feel like I’ve seen another person who says “My files don’t sync properly and no one can figure out why.”

This is why I keep paying for Dropbox.


Thanks for everyone’s thoughts. I did actually come across someone through a friend who had exactly the same problem as me. His was fixed, but neither he nor Apple are sure what fixed it.

The bit that blows my mind is this problem started on one laptop, then appeared on a totally different one (set up from scratch) and survives nuke and paves and multiple different OS levels, all while other devices are perfectly fine on exactly the same network connection.

But hey, I’ve been told it will be fixed. They just won’t tell me when, even after it has shipped. If macOS 12 doesn’t solve it I will either a) use another service or b) see how big a rant I can go on to try and get Apple to take some responsibility. I’ve already had one slightly heated argument with an advisor who would not accept the problem must be on the server end. He was the same one who left the company and did not hand off my case.

1 Like

Apple first dipped their toes into cloud services 21 years ago and iCloud will be 10 years old in a few months. IMO, your only choice is “use another service” because Apple isn’t likely to fix it anytime soon and may never take responsibility. Look how many years it took them to replace the butterfly keyboards and everyone was complaining about that.

Apple is in last place when it comes to cloud services but has started hiring a lot of cloud experts recently. They will get better but it will probably take some time.


Had you ever just logged out and logged back in before trying the change of the Apple ID?

Preach it!
We hear you!

1 Like

I’m not sure, I think I did but actually I only seem to remember the one thing that did it. And to be honest, the email change might have been a coincidence.

The mac Mini is in the process of being nuked right now.

It occurred to me one possibility is that this is not a “two different laptops at different times” problem but a “two Macs at once” problem. It is definitely the case this time around and I’m pretty sure it was the case the first time. It began on the Catalina betas and my Mac mini was in the frame from Feb 2019.

Can’t hurt to hope, though if this fixes it I will have been sitting on the solution from the time I got the new laptop. :sob:

Interestingly enough, I never had issues with iCloud Drive but when trying Apple Notes it was just random sync hell. The worst offender is that you have no means of understanding what is going on.

1 Like

I learned some things while researching this issue. There are different ways apps can use iCloud for “files”. Ulysses was 100% affected by the problem but KeepIt was not. I think I’m right in saying Ulysses uses the old-school approach of writing to a special container that happens to exist in iCloud as far as the OS is concerned, whereas apps like KeepIt (and Notes which was also unaffected) explicitly call iCloud APIs to update their data.

1 Like

In my case there were a lot of issues syncing a huge database of notes (25k) between my Mac, iPhone, iPad and the wife with Apple Notes. For example, I never had an issue with DevonTHINK, which also uses CloudKit. But them DTTG only syncs an index and then downloads the data on demand while Apple Notes seems to try to download everything at once and only while Notes is running (which makes the sync take forever)

I’ve also had my shares of Apple Photos not syncing between devices, but these issues seem to resolve after a couple of hours.

Go figure!

NARRATOR: It wasn’t.

But I am still going to try the log out and in again now. I did leave the laptop powered down for 5 hours today, and that’s over 24 hours since the Mac mini bit the dust. Though I wish I’d thought to actually log out the Mac mini first before I nuked it. Oh well.