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.

Collateral damage.

Generally, by the time iOS beta 3 or 4 rolls out, I can’t help myself and throw it on my carry phone. But I haven’t had time to play this summer. It’s been a particularly busy few months and I needed to make sure my primary phone was as stable as it could be. As such, I’ve been pining away to play with the new Notes app that Apple debuted at WWDC this June. It looks like a tremendous update to one of the built-in apps that could actually change the way I currently use my devices. I’m not alone in these sentiments; I know many other folks in the tech space who are begrudgingly admitting that it’s pretty cool.

Since I’ve been keeping my devices as standard as possible too, I’ve been using Notes between OS X and iOS, even in its current form. I’ve found it to be a useful scratch pad and short-term landing area for little bits of text that don’t even merit creating a new .txt and saving somewhere. And they do sync between devices pretty well (for the most part).

On Wednesday, I’m excited to finally update my devices to iOS 9 and get all the cool stuff I’ve been hearing about, like any other normal user. But something occurred to me yesterday.

When I update my mobile devices, El Capitan is still two weeks away from shipping. Which means that my workflow breaks. If I didn’t have the foresight to think about the disparity in ship dates and extrapolate that one extra step, I’d have been caught scratching my head on Wednesday afternoon as I update and keep working through my day. Like any other normal user.

This isn’t good. For me, or for anyone. But sadly it’s become the norm. Marketing pressure and ship dates trump user experience more and more. Working in software, I understand a great deal more than the average person about how this process takes place and how you don’t always get to make the decisions you want to about the fate of your users when external pressures start exerting force on the business. I know that releasing both mobile and desktop OS updates in the same day is insanity, and I wouldn’t expect that. I know that two dedicated groups of people, working hard to ensure they hit their dates have made every effort they possibly can to make my experience a good one. I know that with the advancements in both operating systems, no decision–no matter how small–is a simple one.

But I’m the end user. It shouldn’t have to matter to me, and it’s not my problem. However, it’s become my problem. What if I don’t want to upgrade to 10.11? What if I can’t? What if my laptop is company-issued and there are no immediate plans to upgrade the OS? My stuff is broken, and I get a big shrug from the company to which I trusted my data. (Which of course, is a much more nuanced and complicated discussion for another time.)

This isn’t the first time this has happened. Apple did this last year with the transition to iCloud Drive. It caused more than a little confusion for both users and developers. But this isn’t just an Apple thing either. Many companies are breaking implicit promises with their users to further push their products into the future, and leaving confusion and doubt in place of a feeling of consistency as people use these products. Apple, of course, has the momentum to carry it forward, and we’ll all forget about this, the way we mostly did when Yosemite shipped and the iCloud Drive transition wasn’t such a big deal anymore. And I fully realize that writing this much because my notes stop syncing (temporarily) seems like absolute overkill. But I spend a lot of my time trying to come up with creative solutions for users so people enjoy the software we produce. I try to solve problems so they don’t have to. It’s the right thing to do. Tim Cook from WWDC 2014:

Apple engineers platforms, devices, and services together. We do this so that we can create a seamless experience for our users that is unparalleled in the industry. This is something only Apple can do.

Software updates have always been risky. I’ve been using computers since I was about five years old, and I know this. I understand it at a level most people don’t. But at this point, with the way software has reshaped our lives, I shouldn’t have to. It’s disappointing that even a company like Apple, so proud of its experiences across hardware and software and delivering the best to its users still falters on these kinds of things. This’ll all blow over. I know that. But it’s a troubling trend, and I don’t have to like it.

PS: It was pointed out to me that iCloud.com will sync/display Notes after the iOS 9 transition. Given the state of the site as an afterthought in almost everything Apple does, I’m not surprised it didn’t occur to me. This will certainly suffice in the time between upgrades, but I wouldn’t have immediately thought about it if someone didn’t point it out. And considering any regular user of iOS probably doesn’t even know that iCloud.com exists as a destination, neither will they.

Things I like this week, volume 13.

Netflix had great success with House of Cards as an original series, at a time when many questioned the company’s future. With the revolving door licensing agreements it and many other streaming services are subjected to, movies will come and go, and users are left wondering. So it began making originals. And HoC turned out to be pretty terrific.

Narcos is a new title in this vein, centered on the rise of Pablo Escobar and the Colombian cocaine trade in the late 70s/early 80s. We’re about four episodes in, but we love it. The writing is great, the actors are great, and the production value is incredible. Told as a narrative interspersed with real footage and photography from the time, it shows an entirely different side of Escobar from the people who were closest to him, and while it’s extremely violent and unflinching in its storytelling, it’s definitely not thin and presents an interesting view of those defining events in law enforcement.

Granted, it could turn to total crap in a few episodes, but that’s why these posts aren’t called “The Greatest Things Ever on Earth”. It’s what’s good this week. If you’re a Netflix subscriber, check it out.

Things I like this week, volume 12.

Apple Lightning Digital AV Adapter
After a summer of traveling and varied successes with Apple TV and the Fire TV Stick for kid videos on the go, I finally slapped myself and picked up Apple’s own hardware adapter.

It’s a small, white, plastic dongle. (Of course it is.) It connects to an HDMI cable. There’s a Lightning cable passthrough so you can charge the device while you watch. It’s almost $50 (insert Metal Gear Solid guard alert sound), but you can get it a little cheaper right now on Amazon.

It pained me to actually admit defeat and buy it, but after talking to a few friends who have one, and now, sitting here, playing a video off my kid’s iPad to the TV at the beach effortlessly, I’m kicking myself for not doing it sooner.