Using iCloud Drive to sync between Mac and Windows?

I’m a long-time, if intermittent, Scrivener user on Mac and iPad. The main reason keeping me from using Scrivener exclusively is that moving between iPad and Mac is key to how I work, and I hate everything about Dropbox – to the extent that I’ve often preferred to drop to a second best writing app rather than using it.

Anyway, here I have a totally different question: for the first time in over 20 years I’m considering buying a Windows laptop.
Now – I know you can get iCloud Drive on a Windows machine. And I remember the L&L staff saying a while back that using iCloud Drive to sync (Mac-to-Mac) was ok and not subject to the technical limitations that, until recently, made iCloud (not drive, just iCloud) syncing not an option. (I was glad to hear that that’s changing in a future version of Scrivener, by the way!).

Has anyone tried using the iCloud Drive folder to sync between a Mac and a Windows machine? With the usual caveats about sync completion, etc, I don’t see why it wouldn’t work – but bear in mind it’s been decades since the last time I used Windows, so there may be obvious limitations that I don’t know. Am I missing something?

It’s certainly possible between computers (not to iOS Scrivener).

WARNING: iCloud can be a little lazy on syncing so ensure any syncing is complete before sleeping or shutting down a computer. It has fewer ‘hiccups’ than it used to.

FWIW, I am ex Apple and use it for backups, storage of seldom used data and shared iWork docs.

I use Dropbox for my Scrivener projects, iCloud, One-Drive for Scrivener backups. I will go back to primarily using Box once they sort out a native Apple Silicon app without having to compromise security settings.

I do not use Google Drive for anythiing.

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How would a person ensure everything in a project is synced, though? Sync time is random, it seems to me, and I don’t know of a way to test for completion.

Google Drive is even worse, in my experience.

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I’m not familiar with the windows interface, but on the Mac end, it’s pretty obvious — there is a little icon next to the folders indicating cloud status. It’s easy to miss because it generally syncs so quickly these days that you don’t really see a pending job.

I use iCloud Drive Mac to Mac and Mac to iOS extensively, and I have for years, and I only have wonderful things to say about it. Never had a problem even though I always throw all I have at it. But windows would be taking it out of its comfort zone, for sure.

If you haven’t had problems with iCloud, you are lucky. Just on 3 December, Howard Oakley published a blog post entitled “What to do when iCloud gets stuck”. Note “when”, not “if”. Howard Oakley even took the trouble to write a utility to help diagnose problems with iCloud (Cirrus – free to download on his site) and I regularly use it when items take too long to sync between my iMac and my MacBook. I certainly don’t have wonderful things to say about iCloud!

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Sounds like this Okley guy has some interest in having people believe that there will be iCloud Drive issues. But I understand, people have different experiences — just the other day I was talking to someone who was absolutely certain, in a matter of fact kind of way, that storing your photos in iCloud means you’ll accept to lose them all when Apple issues an update. There is lots of fake news and conspiracy theories out there. For my experience, which is an n=1 of course, is that over twenty thousand photos are syncing wonderfully across six devices without a hiccup and some ~300GB of data does the same thing. I literally do not recall ever losing any data or photo thanks to iCloud — worst that happened is that 5-6 years ago the calendars and reminders were slow to sync, and to this day the iMessage sync for non-iMessage SMSs is hit or miss. YMMV, of course, but I trust iCloud Drive a million times more than DropBox.

Not at all. Howard Oakley is a former contributor to MacWorld (if I remember correctly) and a programmer who has made available around fifty freeware utilities that can be downloaded from his site. He is also a former Royal Navy doctor, and a painter, who also posts extensively on the history of art. If you take the time to go and look at his site, I think you will realise your assumptions are very mistaken.

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It’s obvious for a file. It’s not obvious for a folder with a thousand files in it.

Not true. There is an indicator for the general iCloud Drive folder (and if you click on it, it will tell you exactly what is downloading and how long it has to go), then you see indicators for each Folder and for each file. You can also enable another separate column to indicate exactly the status of each file or folder at any time. Look at the pictures here to get an idea, I am not on my Mac now so I can’t send screenshots:

Thanks. Not that I’m going to start using it, though!

About 5 or so years ago I used iCloud drive for a while to sync my photos from iPhone to PC. It wasn’t a good experience. The iCloud app on Windows was inconsistent, therefore not reliable. Sometimes it would sync changes immediately and sometimes it would not. I never really knew what it was going to do and when it was going to do it. Eventually I gave up and fell back to transferring photos manually.

The performance of the iCloud app on Windows at that time would have been disastrous for syncing Scrivener projects. Worse even than Google drive, and that’s saying something.

I realize this is a very old data point, so hopefully you’ll receive feedback from someone who’s used the iCloud app more recently on Windows.


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My specific experience with iCloud Drive (iD) involved manual syncs from Mac to iOS Scrivener a couple years ago, in response to complaints about having no alternative other than Dropbox; also iOS 13 utterly broke the sync for a few months, for a number of users. I’d put the project in iD on the Mac, go to the iOS Files app, find the project, and open it in Scrivener from there. Later I’d archive from iOS Scrivener, put the zip file in iD, and unzip it on the Mac. (I hope I’m remembering the steps correctly.)

But, as I’ve indicated already, how long it took to sync changes to iOS (not so bad the other way) was entirely random and there was no cloud icon to tell me if the project was synced or not.

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Actually, that’s not the case at all. He’s a Mac enthusiast. @mbbntu has given you some of his history.

Why did he create Cirrus? He saw that some people (possibly he was, as well) were having problems with iCloud, asked himself if he could make things better and discovered he could. As with the other tools he’s created (each of which includes documentation), he benevolently offered it as free-to-use.

I don’t use iCloud or Dropbox with Scrivener––only use iCloud in a limited way with other things and Dropbox not at all––so I don’t have a bias or knowledge tech-wise either way. But about Oakley’s eclecticlight site––if you run macOS, you’d be doing yourself a disservice to not consider it as a potential primary resource.

Even if you didn’t have a Mac––as I didn’t when I first visited there and will continue to do so when I no longer do––it would still be worth visiting. It’s unique and Mr. Oakley is unique in very interesting ways. He and I are in disagreement about some fundamental premises (mostly unrelated to tech/art) that leak through on rare occasions. With that said, I think he and his site are internet treasures.

I see it’s been answered already.

That all said, until recently I found very inconsistent results with iCloud Drive on Windows, though seems okay now. On Mac it’s been wonderfully consistent for me, though others have experienced issues.

The majority of issues from my time connected to AppleCare were user related, however, even being in a minority can be the most frustrating exercise going.

Well. I got a Surface Laptop to try for myself.
While I haven’t tried using iCloud Drive say to sync Scrivener projects, I experimented a little bit with simple .md files from Typora and iA Writer. As far as I can tell iCloud for Windows (11) is basically broken. Several hours later, the Windows machine hasn’t sent anything up to iCloud yet. There is no manual sync option (that’s the right way — but then it has to work on its own!). Unusable. I’m not even going to bother trying to use it for Scrivener.

In contrast, Dropbox on Windows seems to work rather well, but for me, part of the allure of plugging a Surface Laptop in my Mac ecosystem was precisely to be able to finally get rid of Dropbox and Rosetta 2.
Oh well. I guess Apple is guilty of making their Windows utilities crap to keep people in. Now if only they made a thin-and-large 15” laptop…

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They make a thin and large 16" laptop that blows any Win laptop into the weeds, (and you can run win 11 ARM64 on it)…just saying :upside_down_face:

I have the 2021 16” MacBook Pro, pictured here with the 15” surface laptop 4 that I’ve been trying. I could write an extensive review and comparison but I’ll spare you.

The tl;dr is that the 2021 16” MBP is a radical machine for video-editors and other computing power hungry professionals. I am neither, and I hate the heft and size of it. I need a large-screen laptop but I don’t need a supercomputer. Until two MBP generations ago, Apple made large laptops that were “pro” in name but in fact they were slim and portable. The YouTubers hated them, normal people loved them. Now they released these thick cheeses and the YouTubers are purring. But I, for one, hate it.
The SL4 is a magnificent shell. Hardware-wise it is only let down by a crappy screen, but the real problem is the software. It turns out windows still sucks after all these years. I had bothered to believe those same YouTubers who (probably after a nice check from Microsoft) have been saying that windows was by now comparable to macOS. Nowhere even close.

I hear you. I have a 14" M1Pro which is a screamer and gets away from the heft of the 16" I just sold (2020 model), also have an M1 MacBook Air which is a sweet device, but just a tad short on video editing power (not much).

the hope is the 2022 MBA and/or MacBook Pro 13" will have a fancier screen and just a tad more power in the lighter package. I support the suggestion that a 14/15" MBAir is the next logical step.

…right, because they effectively alienated a whole segment of writers, academics, business professionals who used to buy the 15/16” MBPs for size and not for power. I pray for a 15” MB Air.
I’m intrigued by the 14” too, but by my calculations the vertical screen size (which is what I care about most) ends up being very close to my 12.9” iPad Pro, which has the added bonus of having cellular and pencil writing. So at that stage, I’ll just take the iPad. Similarly with the current 13” MBA: it’s actually a smaller screen than the iPad Pro overall, and dramatically so in the vertical dimension. Microsoft is onto something with their 3:2 aspect ratio here… if only I could hack macOS onto this laptop…

I’ve done some interesting Hacs over the years, but I think I’d be struggling with that one.