It's May 2020. How's iCloud Drive looking?

I’ve been a steady user of Dropbox for years, but after hearing Marco talk about some of the shady stuff they’ve been doing on a recent issue of ATP, I’ve been considering making a migration to iCloud Drive (wherever possible).

(I also needed to locally sync a Dropbox folder this evening. The folder stored about 200mb of content, and I was surprised to hear my laptop’s fans spin up to full blast for reasons that are beyond my understanding as a mere mortal. Why does Dropbox need so much power to sync a — relatively — small amount of data?)

As of May 2020, is iCloud Drive still a minefield? Is Dropbox worth continuing to pay for?

(Consider cost a non-factor, yada yada. For the sake of this discussion, I’d love to focus on reliability, feature set, and creepiness — or the lack thereof.)

I think the “shady stuff” accusation is unfair; really depends on your point of view and what you want/need. Keep in mind Marco doesn’t use even proven 3rd party open source software in his apps and doesn’t use third party app analytics like most other developers do.

Of course, there is his “no tech support, and you’ll like it” attitude too, which is a bit unusual amongst most indie developers that want to please their customers.

Anyway, on the main topic, I would drop Dropbox in a minute if or when iCloud Drive supported selective sync. I have a paid 1 TB DropBox plan that is 90% full and I simply cannot use iCloud as I sync to four different computers and only 1 of them has a 1 TB system drive so my files won’t fit without a lot of manual juggling and I see no benefit to having to do that “just” to use iCloud instead.

Fearturewise, I think iCloud Drive is stable, but no selective sync is a deal breaker for me.


Twice in the past 7 weeks I’ve had to copy a file from icloud to dropbox because it wasn’t syncing (different file each time). Not terrible but annoying because I was teaching online both times & would prefer to have things just work.

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iCloud Drive seems to be working very well for me - across Mac, iPhones and Windows. But there are times that I needed to wait a while before the file is sync, even though all devices are in the same local area network (at home). It’s not as instant as Dropbox yet but I have one less subscription to manage. I already need iCloud for the photos, so it’s no brainer to upgrade to more storage and use the Drive.

I’ve had slow syncing issues too. Files sometimes take a while compared to other services. I use Dropbox selective sync a lot to make sure I have certain files always available on iOS and this is sorely missing from iCloud, although DEVONthink is a nice solution for this. I also need to be able to consistently share to anyone on any device and this is still not working well for me. Aside from these issues, it has gotten much better than it was in the past.

My VPN is always connected and this often causes iCloud Drive not to be able to complete a sync, so I have to disconnect the VPN temporarily.

I’ve been very happy with iCloud drive over the past year or so. It’s solid, and usually gets the job done correctly. There are some sync issues some of the times, but nothing that a good network connection does not fix.
So for me it has replaced dropbox, especially since we now have the option to share folders in lCloud.

Same experience. I’d go as far to say that iCloud is solid as a rock for me. No problems. £6.99 for 2Tb covers my whole family’s storage and their photos. Solid A+


While each iteration of iCloud Drive gets better, I am still not sure it is anywhere near to dropbox from a “it just works” point of view. My entire work life folder lives in dropbox. It is ALWAYS up to date, and updates exactly as I want. I have the 2TB plan (and use about 50%) of it. I just started with the 2TB iCloud plan last month, and am testing it out side by side to test it. The main reason I want the iCloud drive to work is that I am trying to get my iPad as my main work device, and in the integration with iWork suite and iCloud is a little smoother. Dropbox works, but i do end up with a lot of duplicate files when using iWork on iPad. So far, the iCloud Drive is working better for me in this regard, but I am not sure I love it yet for general stability (always syncing on time, finding that there is no longer an offline file when I get on a plane etc). I also feel like it is a lot easier to make a mistake in iCloud drive and delete entire folders. Yes, I can immediately fix it, but I feel like it is too easy on the iPad to click the wrong thing. Obviously I will get used to that. Lastly, I wish there was a smart sync to always force offline files to be offline and the ability to be selective about what they are.

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I have several Macs for different points at my work and most of the work files are on iCloud so sync across the Macs. I have a 2T iCloud plan. I have dropbox also partially due to historical reasons and partially to use it for files I sync with others.

Dropbox syncing is rock solid and fast. It has never failed me. iCloud app synching (with their app specific folder) seems to work ok, creating ones own folder and files on iCloud is a whole different matter. Many apps are not iCloud aware and so if you have the storage optimization turned on and a file your app needs is not actually on your Mac, your app may have an issue. Not an iCloud problem by itself but if this occurs it is not always clear where the problem stems from and before you know it you are fixing something that requires just a download. But the “just download” (i.e. click on the little cloud icon next to file in finder) often times does not work or works very slowly. I have had to wait for some files to come across for many hours. This is such a problem to me that I turned off storage optimization all together.

A few weeks ago my SSD on one of the Macs went poof. Luckily I had a same size SSD and a backup of a week earlier. Funny enough, I have been backing up for many years and this was my first SSD failure (ha!). I had to fudze getting the OS back on the SSD, the backup took a few hours and I was back in business. Not! The backup included my ~/iCloud folder (which maps to the mobile sync folder) and the OS started a reconciliation process between what was just restored and actual on iCloud. Still not a bad thing, however, for some reason macOS started to replace newer files on iCloud with older files from my restore job. That turned into a big mess. Notice that I do have dropbox on the restored machine and dropbox too started a reconciliation process which took all but a minute and deleted nothing from the pool but did copy some missing files from the pool.Exactly as one would expect.

iCloud for phone etc. backup is the bomb, for app specific use seems ok, for general use I have a hard time recommending it.

Wow — thanks for the feedback everybody! So far, sounds like it’s not totally up to snuff. I’d love to consolidate some expenses, but Dropbox has basically always worked (even if it’s been annoying). Switching to a system that doesn’t always work, especially for my job, seems like a mostly bad idea. Thanks all!

I like iCloud Drive. I’ve been consolidating my digital life back to Apple and am transferring all of my document/photos/videos to it. I use it everywhere I can and have had no problems.

With that said I also have a backup of all my files on a WD MyCloud Home and one other physical hard drive. Just in case.

I have had zero problems with iCloud with the exception of the problems I had with syncing Notes when iOS 13 was first released. But, I have two questions:

  1. the only time I now use Dropbox is to share a particular file or files. A common scenario will be that I am speaking at a conference and then after my presentation make slides and other materials available. I can easily share a single document through Dropbox. I don’t believe that is possible in iCloud unless I have a folder and then within that folder a document(s). Am I missing something?

  2. Is it possible to share a DEVONthink file or folder link much like I would with Dropbox and use that as an alternative? I have DEVONthink pro and so it would be easy for me to do this. I just want to make sure that no one would have access to any other parts of my database if I share a link to a file or to a folder. Any input would be appreciated.

Using 3rd party tools and services that aren’t 100% built into macOS or iOS, as you mention, has important benefits when the system itself has to be recovered.

I prefer my mission critical files and photos to be in a system/service not intimately tied to the same OS and AppleId. It’s another level of backup/security being protected against a software flaw or OS issue propagating through everything.

I tried using iCloud Drive for a few months, and then ditched it for storing everything in GitHub and accessing it on iOS using Working Copy. A couple reasons stand out:

  • Being a Terminal user, having the actual location of iCloud Drive in an obscure location of my Mac caused a few random issues.
  • Sync wasn’t always reliable.

I’ve been using iCloud Drive instead of Dropbox for a few years now, and I think I’m still waiting for a few things to sync… That’s how it’s been for me lol…

Sharing with DEVONthink 3 you would need the server component. It works well and access limits can be set up. Up to you to determine if it is worth the extra cost.

That and there is value in testing a backup’s recovery from time to time but who ever does that? It would be nice to know if there is a recovery “simulator” which would just indicate which files would have been left out/failed to recover.

I now exclude iCloud from the back up. It is silly of me to have included it in the first place because these files are in essence backed up by Apple. Although I do create an iCloud back up of sorts with Hazel but that is more to make sure I have access to project files and such during the time a restore job takes place.

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Thanks, I don’t think I want to spend the erred money. :moneybag:

I do. Any time I make a change to my backup system, I run a test backup and restore. Then I verify that the restored data is good. After that I restore and verify a few files from each source every month or two. If I’m going to pay money to backup my data, I’m going to do my part to insure it’s there when I need it.

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