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Moving to iCloud Drive

When iOS 8 came out last month, those of us who installed it found our iOS devices asking us whether we wanted to upgrade to Apple’s new iCloud Drive service. Adam Engst advised that “when iOS 8 asks you to upgrade to iCloud Drive, tap Not Now” (see “iOS 8 Users: Do Not Upgrade to iCloud Drive, 16 September 2014).

Why? At the time, OS X 10.10 Yosemite was presumably a month from release, and 10.9 Mavericks was incompatible with iCloud Drive. Also, as Adam put it, iCloud Drive is “a one-way street — once you upgrade, you can’t go back to the old document-and-app-specific approach that’s compatible with Mavericks.” Users not running a developer preview or a public beta of Yosemite would find their iCloud documents inaccessible on their Macs if they accepted iOS 8’s kind offer. Particularly annoying, though, was that the same day that iOS 8 debuted, all the iWork Web apps at made iCloud Drive a requirement.

This left users who used iWork apps on their Macs, their iOS devices, and in their Web browsers facing a dilemma: no matter which way they went — whether enabling iCloud Drive or not — they would find one of their avenues of getting iCloud documents blocked. The matrix of accessibility was complex.

That was then.

Now Yosemite has descended upon us from on high, and the time has arrived when the majority of Mac and iOS users will want to revisit Apple’s iCloud Drive upgrade offer. As an early adopter (with the scars to prove it), I have already done that: a week ago, I installed the “golden master” of Yosemite on my iMac. With that final piece in place, I enabled iCloud Drive.

In my case, I had no choice but to do it and hope for the best. I need to revise “Take Control of Pages” to match the new iCloud Drive reality that Apple has imposed on us. Fortunately, the transition went well… for the most part.

What Worked -- As I expected, my iWork documents appeared in the iWork Web apps on just as they had before the transition. Moreover, also offered a new iCloud Drive file browser that made managing iCloud documents much easier.

Pages for Mac also took swimmingly to iCloud Drive, employing a new, much more Finder-like dialog for opening documents, with sidebar items for accessing Pages documents in iCloud, any document in iCloud Drive, or any document on the Mac.

And, of course, the Yosemite Finder made iCloud Drive an equal citizen with all of my Mac’s local folders and mounted volumes.

As for my iOS devices, my aged iPad 2 and new iPhone 6 Plus presented my iCloud documents as they always had in my iWork apps. For those apps, on my iPhone and iPad at least, the transition was transparent, though it did take a number of minutes for each of the devices to sync documents with iCloud Drive (I have about 60 Pages documents in iCloud, some of them rather hefty).

What Didn’t Work -- My iPad Air, on the other hand, was not so lucky. At first, the documents in the Documents browser in Pages seemed to be syncing with iCloud, but not very well: some synced, some didn’t, and some stalled midway in the syncing process. In fact, those documents that stalled never finished syncing. Moreover, if I changed a Pages document that had synced to my iPad Air, those changes never synced back to iCloud Drive.

I tried to convince my iPad Air to accept the iCloud Drive updates in several ways, all to no avail:

  • I first disabled iCloud syncing for Pages so that there were no documents shown in its Documents browser, and then re-enabled iCloud syncing (Settings > Pages > Use iCloud). The documents started to sync, but then they stalled and the syncing never finished, as before.

  • I next turned off iCloud Drive on the iPad Air (Settings > iCloud > iCloud Drive > iCloud Drive), told Pages to discard the documents that it had, and then re-enabled iCloud Drive. Once again, I got a partial sync and a stall.

  • After backing up all of my iWork documents that were stored in iCloud Drive to my Mac, I performed the dreaded Reset Settings on my iPad Air (Settings > General > Reset > Reset All Settings; see this MacRumors post as to why this is “dreaded”). All the reset succeeded in doing was deleting my lock screen and home screen settings, resetting my ringtones to defaults, and disconnecting my current Wi-Fi connection. Pages on the iPad Air still persisted in not syncing.

(Note: it’s very easy in Yosemite to back up your iCloud Drive documents to your Mac — in the Finder, just drag them from iCloud Drive to a local folder.)

Anyway, three strikes and I thought I was out — that is, I figured my next move would be to completely wipe my iPad Air and set it up as a new device.

Fortunately, before I took that drastic step, I tried one other thing.

What Solved the Problem -- What finally got my iPad Air to join the iCloud Drive party was this: I signed out of iCloud on the iPad Air (Settings > iCloud > Sign Out) and then signed back in.

Signing out got rid of all my iCloud data on my iPad Air (including shared photos, contacts, and so on, as well as the documents in my iWork apps). My iPad Air and iCloud (not just iCloud Drive but all of iCloud) had become complete strangers.

Signing back in reintroduced my iPad Air to iCloud, and, in the process, my shared photos, contacts, and everything else iCloud-related all synced with the device — including the documents in my iPad Air’s Pages app.

Now I have iCloud Drive working on my Mac, in my Web browser, and on all three of my iOS devices. When I make a change to an iWork document on any of my devices, those changes propagate quickly to my other devices (though not instantly — it sometimes take a minute or two for an updated document to sync on another device when I open the iWork app on it). Once again, everything just works.

Yosemite is now upon us, and if you are an iCloud user and you upgrade to Yosemite, you won’t be able to avoid iCloud Drive. In most cases, your documents should weather the transition intact, but if you also have an iOS device and you discover that iCloud Drive misbehaves on it in any of your iCloud-enabled apps, do the simplest thing first: sign out of iCloud on the device and then sign back in. This simple act might well brighten up an iCloudy day.


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Comments about Moving to iCloud Drive
(Comments are closed.)

M. Perry  2014-10-15 20:44
You said: "iCloud Drive is “a one-way street — once you upgrade, you can’t go back to the old document-and app-specific approach that’s compatible with Mavericks.”

That sounds scary almost beyond belief. Does it mean all the documents and apps on my Mac or just those I choose to synch via iCloud and a specific app?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-15 20:53
All the documents you have stored in iCloud. Not the documents you have stored locally on your Mac.

The Apple support document at provides more details.
Mark R. Williamson  2014-10-16 00:08
You said, "Yosemite is almost upon us, and if you are an iCloud user and you upgrade to Yosemite, you won’t be able to avoid iCloud Drive."

Another scary issue. What about iCloud users who need to move some Macs to Yosemite and leave others on Mavericks (or Mountain Lion)?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-16 00:20
You won't be able to access iCloud documents from the iWork apps on Macs that aren't running Yosemite. You will be able to upload and download iWork documents from those Macs using the iCloud Drive web app in Safari. And yes, I know, it's an incredibly clumsy and inconvenient workaround.
barefootguru  An apple icon for a TidBITS Contributor 2014-10-16 19:14
Or presumably edit them directly using the iCloud (Safari) versions of the apps.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-16 19:18
Certainly. However, the web apps offer reduced functionality (e.g. you can't create new paragraph styles for Pages in the web app). Still, that is an option for basic editing needs.
Steve Simnett  2014-10-17 11:57
Okay, so I am sitting looking at this message, "When you upgrade to iCloud Drive, the device below (actually an iPhone 4), will not be able to access the documents currently stored in iCloud ...
Actually, I do have other devices, but use my iPhone 4 abroad.
So my question is, will my old iPhone 4 become basically defunct from being able to access stuff I created on Pages, Numbers etc. ie). It wont be able to see any docs at all.
Steve Simnett  2014-10-17 12:10
Sorry, Just read this ...
I guess my iPhone 4 becomes less productive :0(

What if I already upgraded to iCloud Drive but still have devices with iOS 7 and OS X Mavericks?

You won't be able to use iCloud Drive on these devices until you update to iOS 8 or OS X Yosemite. If you already upgraded your account and need to use a device that doesn't support iCloud Drive, you can still work on your documents locally, but they won't be kept up to date with documents on your devices with iOS 8 or OS X Yosemite
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-17 12:11
It won't be defunct, but it won't be able to access your iCloud Drive documents. However, you can still create and edit documents locally on the iPhone 4 when you travel, and transfer them to your Mac via iTunes, or by sending them as email attachments when you return home.

Also, before your trip, you can transfer the files you want to work on while traveling from your Mac to your iPhone 4 using iTunes. Read the Apple Support document at for more.
Steve Simnett   2014-10-17 12:47
Thanks Michael. Nice article by the way.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-17 13:01
Glad to help.
darren  2014-10-18 17:35
I have an additional question: Does upgrading to iCloud Drive affect how other data syncs? e.g. iCloud Keychain, Contacts, Reminders, Safari bookmarks, keyboard shortcuts, etc.

I'm still using an iPhone 4 and have an older MacBook Pro running 10.7, so updates to iOS 8 and Yosemite aren't a possible path.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-18 19:44
I don't know. I don't *think* iCloud Drive affects access to synced data (as opposed to synced document), but I don't know this for a fact. I suggest you not upgrade your iCloud account to iCloud Drive until more information is available.
darren  2014-10-18 22:43
Thanks, Michael… that's exactly the assumption i'm working under until i get more information.
I installed Yosemite on my laptop but have not engaged iCloud drive. I have Mavericks on my iMac, OS 8 on my iPad but OS 7 on my iPhone 4S. Pages no longer syncs with the Laptop but other apps do like Notes, Calendar and Reminders. Will these other apps continue to sync across all 4 devices if I engage iCloud drive on my Laptop? I would like to upgrade the iMac to Yosemite but do not want to lose the ability of the iPhone 4 to sync on notes and calendars
John Tenny  2014-10-17 23:36
I just installed Yosemite and found the iCloud Drive in Favorites. Thinking I could drag from there to the desktop, I did just that. That deleted from Favorites and now I can't find it anywhere. Where is the original folder located?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-17 23:40
There is no "original" folder in the sense that you mean, nor can you put iCloud Drive on the Desktop. However, you can get iCloud Drive back in your Favorites sidebar: Choose Finder > Preferences, click the sidebar icon in the Finder Preferences window, and enable iCloud Drive in the list of sidebar items.
This just saved my neck. Thank you!
So I was one of those who took apple up on their offer to enable iCloud Drive when I upgraded to iOS 8. I had no choice then, but to continue composing documents on my Mac in Mavericks. I am now concerned that those documents will be lost in translation once i upgrade to Yosemite. You think this is a valid concern?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-18 12:09
I can't say for certain, because I don't have your Mac in front of me, but if the files are stored locally on your Mac, enabling iCloud Drive should not affect them.
Carsten Schmittmann  2014-10-18 12:50
Thanks a lot Michael for your article. It really helped me save my day (half of the night had already been spent on the problem). Having solved my direst problems I dug deeper as all my data that had been saved to the iCloud on iOS 7 and Mavericks using the appropriate apps (GoodReader, PDF Export etc. resp. the hidden /Library/Mobile Documents folder) had GONE! First I looked up whether the MoDoc folder still exists. It does, but there is no way looking into it! So I applied Time Machine and retrieved 2 PDFs. As it is TM habit it retrieves the data where they are from. But again I was not allowed to open the MoDoc folder in /Users/Library. So first I used Spotlight and by clicking on the results I was taken to the retrieved data in the GoodReader folder. And in addition all the formerly created app-folders could be seen for a moment. But nevertheless, the files within the folders are gone. This is not a professional behaviour by apple. I am really disappointed.
Is there a way to have remote folders only? with dropbox I can decide which folders will sync with my mac, I can't find a similar option with iCloud drive.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-19 10:53
No, there is not. iCloud Drive is not a replacement for Dropbox. iCloud Drive is designed to present the same content across all your devices.
iWorks on my iMac running Yosemite creates an updated Pages file in iCloud Drive but that file cannot be seen by Pages in nor updated Pages on my iPad2 (file created only seen on iMac, in other words iMac created iWorks file won't sync across iCloud Drive to iOS8 nor iMac iWorks does see files created in and iPad2.
Benjamin Lowengard  2014-10-20 17:53
Seems like just yesterday I had a syncing mounted folder on my mac and Apple said: we're not gonna do THIS anymore. Now Apple wants me to have a syncing (mounted) folder again. What goes around comes around?
ljwink  2014-10-21 08:24
I don't use any of the iWork apps. What does iCloud do for me? What, beside iWork apps, can be 'shared' between my Macbook Pro and iPhone 5?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-21 11:36
I see apps like 1Password, PDFPen, iMovie, and GarageBand using it, among others. I suspect many more apps will follow.

Note, by the way, that iCloud Drive also allows you to share files with other Macs that are logged into iCloud with the same AppleID…and the iCloud Drive Web app makes it possible to get at your iCloud Drive files from any computer with a modern Web browser.
William Dickenson  2014-10-21 09:32
I updated my iMac and laptop to Yosemite and my iPhone to iOS 8. I left my iPad 2 at iOS 7 due to performance issues. If I now move to iCloud Drive will I still be able to sync calendars and contacts with my iPad?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-21 11:29
As I responded to Darren in this same comment thread, I don't think there will be a problem, but I don't know that for a fact. If you want to be prudent, wait a week or two and see if there are any definitive reports that would clear up this uncertainty.

Or you could simply try enabling iCloud Drive on your iPhone and see what happens (I believe iCloud Drive is enabled by default in Yosemite, so you've already crossed the Rubicon there). The worst thing that can happen is that your iPad 2 running iOS 7 won't sync calendars and contacts with your other devices, meaning you'll have to update your iPad 2 to iOS 8 as well. However, as an iPad 2 owner myself, I can tell you that while iOS 8 runs in a very leisurely fashion on an iPad 2, it does run well enough that I haven't regretted updating mine.
Dirk Roorda  2014-10-21 15:39
As a test I copied a folder from my Dropbox into iCloud Drive.

The folder has 1 GB of data and has some deeply nested subdirectories.

After it entered the iCloud Drive folder, nothing much happened. I have a fast internet connection (6 MB/s), but not more than a few KB/s were used in the following hours.

Through the website I saw that some subfolders existed on iCloud Drive, but there was no way to tell what material had been uploaded and what was still waiting and how long I had to wait. I did not see any network activity.

Contrast this with Dropbox: it does the job, unattended, without giving me uneasy feelings, and Dropbox gives a detailed account of the sync status of all files at any time.

For my own peace of mind, I decided not to look at iCloud Drive for many months to come. A promise with no fulfillment.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-21 15:46
Let me repeat this: iCloud Drive is not a replacement for Dropbox, and was never intended as such. Its primary purpose is to allow apps to create and manage their own cloud-based file collections across devices, yet give users the ability to get at those files outside of the app if necessary.
I had thought that iCloud Drive could replace Dropbox, but I'm starting to think you're right. I have to wonder why then Apple offers plans with up to 1 TB of storage if all iCloud Drive is supposed to do is share files between iCloud-enabled apps?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-10-26 21:33
Apps like iMovie, Pixelmator, and GarageBand can produce rather large files. And once you start storing your photo library, iOS device backups, and so on…well, a few hundred MB here, a few there, and pretty soon you're talking about real storage! 😄
Ramoelc  2014-10-31 07:07
hey, I got a question, I got a SSD as my primary drive for yosemite, but doesn't have much space and I don't want to use almost 90% of the space of my drive for photos, how the iCloud drive works, fi I upload my 20 gb photos to iCloud, will it take my drive space, if so, how I change for a second hard drive? if not iCloud drive will never work for plp that have a low space SSD for OS.
Jeezlouise  2014-10-21 15:46
I upgraded to Yosemite the day it came out. I'm not "techy" so not sure if I chose the ICloud drive or not. :( However I did a shut down of my computer last night and then this morning after re-booting (slow!!) found that all my contacts are missing! They're in ICloud but not in my MacBook Pro.
The Windows version of iCloud Drive allows me to put an iCloud Drive on the desktop. I've not found a way to do it on Yosemite.

Anyone found a way?
KevinG  2014-10-26 16:59
My Hidden /library/Mobile Documents folder still showed in the finder (where I had made it visible) but showed empty.. however when I went there in the terminal app.. everything was still there
Had same problem with iPad Air, NOTHING worked. Have repeatedly signed in and out of iCloud Drive, deleted device from devices list on iCloud account, deleted iWork apps from device, etc. Calendar, Contacts, Notes sync correctly. Other apps (MindNode) which WERE working with iCloud, now are not. And Pages/Numbers/Keynote continue to be on an iPad island. iPhone 5s configured to same account is working correctly, as is iCloud on the web. This is a nasty bug and I'm completely stumped.
James Tummins  2014-11-01 19:18
I'm having the same persistent problem with iCloud. I thought it was isolated to iWork apps, but recently discovered that Safari pages are not available on other devices that do have access to iCloud (iPhone, MacBook Pro).
Ramoelc  2014-11-03 11:01
hey, I got a question, I got a SSD as my primary drive for yosemite, but doesn't have much space and I don't want to use almost 90% of the space of my drive for photos, how the iCloud drive works, fi I upload my 20 gb photos to iCloud, will it take my drive space, if so, how I change for a second hard drive? if not iCloud drive will never work for plp that have a low space SSD for OS.
Michael Montgomery  2014-11-05 10:42
Please help. I want to move PDF files to iCloud Drive so I can view them from iPad Mini and iPhone 5s. Both are up to date. I was able to move the docs from my Mac to the iCloud Drive folder, but how in the world do I access and view them from my phone? Seems like there should be a Finder App for iOS 8. I can't see where anyone else has brought up this issue on the internet. An Apple Forum suggested dowloading Documents 5 from the App store. Thank you!
iOS 8 on a 5C, new Yosemite on the Mac. Tried to turn on iCloud Drive: fine on phone, but just keeps spinning at "setting up" on the Mac. Hours by now...
kaitlin   2014-11-09 11:08
Does upgrading to Yosemite affect my Macbook's memory in anyway or wipe out my existing documents? I just want to update my Mac directly without the hassle of backing up with an external disk drive.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-11-09 12:39
I couldn't possibly answer this question without knowing a great deal more about your specific setup. I strongly recommend you consult Joe Kissell's book, "Take Control of Upgrading to Yosemite."
kaitlin   2014-11-10 03:08
I got my Mac not long ago so it's the 2014 ver running on the latest Mavericks. There's nothing much inside, just basic files, songs, videos.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-11-10 11:15
I will NEVER recommend you update a Mac to a new version of OS X without making a backup first. Chances are very good, of course, that the update will be successful, but there is always a small chance that it won't. A backup will help you recover your data if things don't go as they should.

Similarly, I haven't been in a serious auto accident in decades, but that doesn't mean I don't wear my seatbelt each time I get into my car and drive somewhere.
Ramoelc  2014-11-10 20:47
Sorry I didn't get a response for this question, so I'm trying again. I got a question, I got a SSD as my primary drive for yosemite, but doesn't have much space and I don't want to use almost 90% of the space of my drive for photos, how the iCloud drive works, fi I upload my 20 gb photos to iCloud, will it take my drive space, if so, how I change for a second hard drive? if not iCloud drive will never work for plp that have a low space SSD for OS.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-11-11 02:16
You are confused about what iCloud Drive is and what it is for. Its primary use is for applications to store their documents in the cloud so you can access those documents from your various Apple devices. Usually, those applications store local copies of the documents on each device, but sync those local copies with the ones stored in iCloud Drive. As far as the documents used by iCloud-enabled apps, you don’t save any local storage by using iCloud Drive because of the locally cached copies.

iCloud Drive also lets you copy your own files to it so you can access them from different Mac and iOS apps, but, even then, if you manually copy your photo files to iCloud Drive, you won’t free up space on your Mac because iCloud Drive will try to keep local copies of those files cached on your Mac.

Apple also offers a service in iOS 8, currently in beta test, called iCloud Photo Library, which stores all the photos from your iOS devices in iCloud. This could free up space on your iOS devices, but it isn’t yet available on the Mac.
Ramoelc  2014-11-12 10:30
ok, its exactly the iCloud photo library that I’m concern about, when its available for mac, it will stored all photos on the library into my hd as a cache? I mean, I have 20 gb of photos, so I’ll have 20 gb as cache in my hd, can I change the cache folder. I dont have 20 gb available in my OS X ssd. do you know what i meant? thank you
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-11-12 12:42
Inasmuch as Apple has not yet released the new Photos for Mac app, I can't tell you how it will work in terms of storage on your Mac. Like you, I'll have to wait until Apple releases it to find out.
Richard Partridge  2014-12-12 19:06
Many thanks for the above. Our nice new iPad Air 2 wouldn't sync Pages documents with the iMac (still on Mavericks), though the iPhone (also on iOS 8) would. Logging out of iCloud and back again did the trick.
So in fact you can use iCloud with an iPad on iOS 8 without having to use iCloud Drive.
Michael E. Cohen  An apple icon for a TidBITS Staffer 2014-12-15 14:37
Yep, that's true—but only as long as you haven't activated iCloud Drive in your iCloud account on any of your devices or at