hoakley March 27, 2018 Macs, Technology

Solving problems with iCloud Drive

Yesterday I was a bit scathing over published solutions for problems with iCloud, specifically the common problem of protracted or failed synchronisation of iCloud Drive. You dragged some files to iCloud Drive five or more minutes ago, and they still haven’t been synced to it.

So what are Mac users recommended to do when this happens?

Apple has several articles which touch on this issue, but most of them duck syncing problems. For example, Apple’s list of suggestions for problems using iCloud offers the following steps:

make sure your Mac has a “strong Internet connection”;
check Apple’s status page;
update to the latest release of macOS;
ensure you’re signed in using the correct Apple ID.

Apple does provide a more specific set of suggestions in another article, headed What if my files don’t update to iCloud. These include:

ensure that you have enough storage;
sign into iCloud on all your devices and enable iCloud Drive;
ensure you have an active Internet connection;
install latest versions of Pages, Numbers, Keynote;
create a new document and save it [to iCloud] to see if it uploads to iCloud. If it does, see if other documents start uploading;
if those fail, contact Apple Support.

There is a lot of third-party advice, from vendors of products which rely on iCloud Drive, and from ‘independent’ support sites including the press. A collation of suggestions drawn from these includes:

turn iCloud Drive off, then back on again;
restart your Mac;
verify that the correct time and date are set;
check that iCloud is not being blocked by a firewall;
sign out from iCloud and back in on all devices, although this may disrupt services such as Apple Pay;
in spite of trying these, sometimes it takes up to 72 hours for iCloud to propagate new files/folders.

Pooling all this advice, a wise sequence to try in the event of problems getting files to upload to iCloud Drive, or to appear on iCloud Drive, might be:

check Apple’s status page, as you won’t get anywhere if there are service problems;
run generic checks on your internet connection, etc., to ensure there is no connection problem, and ensure that you have sufficient free space on your iCloud Drive;
check your Mac’s date and time are correct, as significant discrepancies will cause problems;
try uploading a small file (particularly if you are waiting for large files to be uploaded);
consider contacting Apple support.

I have been unable to discover any suggestions based on insights into how iCloud works, methods for establishing where the failure is or its cause (even a cryptic error number), nor more specific remedies which can be attempted. All recommendations treat iCloud and iCloud Drive as an impenetrable Black Box. EtreCheck and other diagnostic utilities do not attempt to examine iCloud Drive in any detail, nor to establish the health of its service.

If you have more knowledge or better experience, please let me know, preferably in a comment here.

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1

jaydisc on March 27, 2018 at 11:11 am

I decided to take iCloud Drive for a spin in June 2016, but I needed a way to test its reliability before committing heavily to it, so I decided to try using git to track the folder’s contents. Specifically, I initialised git inside ~/Library/MobileDocuments/com~apple~cloudDocs, which is really just the contents of iCloud Drive that ARE NOT part of any Application’s folder inside it. I did not want the git repo itself to be synced, so I used the –separate-git-dir argument with `git init` and stored the repo outside of iCloud Drive.

1.75 years later, it’s been remarkably successful, with one minor exception. I had Finder aliases inside the iCloud Drive folder pointing to other files also inside the folder, and those aliases were broken on any other device but the Mac they were created on. Other than that, it’s worked flawlessly. At the beginning of every month, I use git to see what’s changed and commit the changes and return again the following month.

Based on how reliable iCloud Drive was for me, as well as the methodology I had used to validate it, I did the same with iCloud Photo Library. iCloud Photo Library shined similarly to iCloud Drive with no problems to date. On a completely new MacBook, I downloaded a fresh copy of that Photo Library and compared it to the git repo. Interestingly, while the folder structure inside Masters was NOT identical, git automatically tests for “rename detection” which can identify if the same file has been moved elsewhere in the same repo, and while some of Photos’ Masters were inside different sub-folders, every master photo was present, accounted for, and unmodified.

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- 2
  
  hoakley on March 27, 2018 at 11:23 am
  
  Thank you – valuable experience to pass on here, thanks.
  Finder aliases are host-specific, so they will work across normal file-sharing, but not via any cloud service, as far as I am aware.
  Some expert users have reported many problems when trying to upload files, or with the propagation of uploaded items to other connected systems, which is the reason for my interest here. What do you do when, half an hour later, those files still haven’t synced?
  No one seems to have an effective answer.
  Howard.
  
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3

Alrescha on March 27, 2018 at 2:21 pm

For me, the short answer is to kill cloudd. It will auto-restart.

The problem seems to be that if cloudd encounters a network problem, it just stops working. Mobile users who sleep their Macs may never see the problem as waking the Mac may also wake cloudd.

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4

Michael Tsai - Blog - Solving Problems With iCloud Drive on March 27, 2018 at 3:35 pm

[…] Howard Oakley: […]

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5

kazB on August 8, 2018 at 3:16 am

My experience of uploading documents/files to iCloud has been deeply disappointing. Although the files seemed to have been uploaded successfully before I turn off my work Mac (no cloud beside the folder in iCloud list view), when I try to access these from home they have not uploaded and cannot be accessed (folder with arrow in list view). I can wait days for the upload to complete. Home Mac is never turned off, so not a ‘wake up’ issue. These issues mean that I have not been able to relinquish my Dropbox account, which is deeply annoying. I would be grateful for any advice!

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  hoakley on August 8, 2018 at 10:41 pm
  
  Sorry to be so slow to reply.
  Have you used Cirrus on both the Macs?
  What I’d do is run Cirrus’ little upload test on each, watching the circular progress indicators, and having a look through its log excerpt. There are several articles here which explain how to use features in Cirrus, and it has a full Help book too.
  This is easiest if both Macs are side by side, which you obviously can’t do. If your work Mac uploads fine, then I would get an idea on download by making a screenshot on a connected iOS device, and saving it to your iCloud Drive folder there. watch the progress indicator on the Mac: it should appear fairly soon, and make that new file available. You can also run the Cirrus test on it.
  Which version of macOS are your Macs running? Are they also doing a lot of other things on the internet at the same time? iCloud schedules its sync activity at low priority, below almost every other connected task, so readily gets delayed. And there’s no way to change that.
  Howard.
  
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