iCloud Drive, Finder, and missing folders.

09-23-2015, 1:55 PM
For about the past two months, I’ve been exploring iCloud Drive as a single destination for my working data. I’ve realized that support for it within apps is coming along quite nicely, and I’m already paying for the storage (photos) so why not give it a shot? Since paring back what I keep online in favor of storing at home on my Synology, the total set of data I’d want access to is minimal. Add in iOS 9’s iCloud Drive app and I’d probably be able to get by just fine.

Let’s get something out of the way right now. Many of you are pulling your hair out now, screaming “JUST USE DROPBOX” at your screens. I have been a paying Dropbox customer for seven years now. It’s an amazing tool and has changed the way I use computers. But for the purposes of this experiment, it was an extra point of friction. The goal was to have things be as “normal” and seamless as possible between devices, as a typical user of Apple products and services might experience. And the truth of the matter is that for weeks, it’s been a seamless, enjoyable process, to my great delight and surprise.

I was using iCloud Drive between my 2014 MacBook Pro, my iPhone 6 Plus, and my iPad Air 2. All updated to latest software releases, and all talking to one another consistently. I had built a few new workflows to account for the quirky ways iCloud Drive handles and sequesters certain files in app-based folders, and was pleased with the results.

Yesterday, I restored my former 2013 MacBook Air to a clean Yosemite install and signed in to iCloud. And some of my folders were missing in iCloud Drive. Folders that had been specifically created by apps (Drafts, Scanbot). Every other folder that I created myself and to which I uploaded files was there, and their contents accounted for. Only app-created folders were missing from this machine. So I began testing.

  • I tried restarting, to kick the iCloud Drive sync services again, multiple times. No joy.
  • I tried relaunching Finder via the Force Quit menu, multiple times. No joy.
  • I tried signing out and back into iCloud. No joy.
  • I tried adding files to those folders via my other Mac to perhaps nudge them into existence. No joy.
  • I tried adding files via the connected iOS apps, same rationale. No joy.
  • I thought that it might be that there were no OS X counterparts to those apps (Pixelmator, for example, showed up fine), but this didn’t seem reasonable, as they’re working on another Mac anyway.
  • I tried deleting the folder and the iOS app, reinstalling and recreating the folder, to see if this was tied to the actual creation event. Worked on the MBP, not on the MBA. No joy.
  • I tried creating a folder on the affected system with the same name, wondering if it might “find” the missing folder. No joy. Now I had two “Scanbot” folders.
  • I added a completely new, previously unconnected iCloud-based app (iA Writer Pro) to see if a new folder would be generated. Worked instantly on the MBP, nothing on the MBA. No joy.
  • I tried physically connecting my iPhone, thinking this might have something to do with the “Trust this computer?” dialogue. No joy.
  • I tried syncing my iPhone through iTunes. No joy.

At this point, having read plenty of discussion threads and FAQs on Apple’s site, I’m giving up. The files appear correctly on iOS (iCloud Drive app), on the web at iCloud.com, and on my MacBook Pro, as it’s the computer I’ve been using. These app-based folders remain missing on the MacBook Air. The problem isn’t iCloud Drive – it’s doing exactly what I expect it to (surprisingly well and quickly, I might add). The problem is with the Finder integration… on certain Macs.

I noticed the same issue on my Mac mini, which made me wonder if this could be related to older hardware. This seemed unlikely to me, but it’s the only thing I can think of that would set these machines apart. The only difference I can see across these three computers is their age.

So what about them is causing them to not be able to see these folders? I’m at a loss, and in the process of moving some files back to Dropbox because I need access on OS X and can’t seem to get it. I would genuinely appreciate any assistance, tips, or otherwise constructive ideas. iCloud, for all its improvements, remains a black box. My experience with it has been better than most, and I’ve truly enjoyed its ubiquity the past few weeks. But I need it to work everywhere for it to work at all, so I’m stuck.

09-23-2015, 2:43 PM
I shit you not, the Drafts folder just appeared. Scanbot is MIA.

09-23-2015, 3:00 PM
Scanbot is back.

I don’t know how to feel about this. iCloud is like a variation on ‘the Aristocrats’.

09-26-2015, 8:21 AM
So I’m pretty sure that the missing folders issue is a byproduct of massive network activity during background processes related to iCloud Photo Library. This was suggested to me by my friend Sam as he mentioned noticing some similar weirdness. I was monitoring iCloud Photo Library activity as it was ongoing, but there are perhaps some processes that (like everything else with iCloud) are fairly obfuscated to the user, sucking up network connections and saturating them even after things seem complete.

It makes sense, but it’s still kind of weird to me that file operations wouldn’t be prioritized over photo operations. Some of them seemed to be, since 95% of my iCloud Drive content showed up quickly, but something held up those iOS-related folders for some reason. I guess the takeaway from this exercise is to ensure all your iCloud Drive content shows up first, and then enable iCloud Photo Library if you’re using it. Next time I set up a Mac, I’ll be sure to do it in this order, and hopefully the arcane incantations I performed this past week will be a distant memory.

The whole purpose of going all-in on Apple apps and services is because I’m trying to use these devices as a normal user would, deriving the integration benefits and ease of use Apple offers. But being the kind of person I am, it’s tough to shake the need to debug a problem like this. Had I just waited, evidently everything would have sorted itself out. Perhaps there’s a lesson in here for me somewhere beyond the setup order I’ll use in the future.

Author: Seth Clifford

I'm here for the open bar.