By Dan Moren

October 4, 2023 12:54 PM PT

Bitten by the black box of iCloud

iCloud is, when you think about it, kind of a thankless service. At its best you don’t notice it—everything, in the unofficial mantra of Apple dating back decades, just works. Your data is in sync across all your devices, changes update immediately, and you never get a single error message.

The thing is, like a lot of Apple tech, it’s a black box. Data goes in, data goes out. What happens in the middle…well, shrug. You just put your faith in the fact that what’s working will keep working.

But as anybody who’s ever tried to troubleshoot iCloud problems can tell you, when it goes wrong, trying to fix it is an exercise in frustration—as I learned recently, in a particularly spectacular fashion.

Intermittently cloudy

At about 9am Eastern this past Monday, my connection to iCloud went kaput. I first noticed the issue on my MacBook Air: my iCloud mail wasn’t being fetched, messages that I read or deleted were popping up again, and I couldn’t access files in my iCloud Drive.

At first blush, my other devices seemed to be fine, leading me to conclude that there was some specific issue with iCloud on the MacBook. I chalked it up to some weirdness with having reinstalled the final version of Sonoma atop the beta, and started off on the usual troubleshooting steps: quitting apps, restarting, and then the big guns—logging out of iCloud.

That’s the point where things went truly amiss. While I was nominally able to log back into iCloud, most of my data wasn’t actually syncing back. A dialog box told me that I needed to verify my account in order to re-establish end-to-end encryption for sensitive information like my keychain and health data, but clicking the prompted button did…absolutely nothing.

At this point, I delved even further, restarting my Air into recovery mode and running Disk Utility to see if there was an issue there.

But at some point during this process, I noticed my other devices were likewise having issues with retrieving mail—the top message in my inbox remained steadfastly from just before 7am. Other services, like Find My, were totally dead, refusing to show me any information. Even third-party apps that rely on iCloud to provide syncing—Ivory, for instance—had issues. Attempts to log in to iCloud.com via multiple browsers and devices all came back with a connection error.

So I visited Apple’s System Status page, which purports to show the state of all of the company’s network services, reasoning that I couldn’t be the only person experiencing such strange behavior. But the indicators there were all green, and casting about on social media didn’t yield the cascade of reports I’d expect to see if iCloud were down (nor had anything surfaced on the Apple sites I frequent).

As someone who spends a lot of time working with technology and did his stint in tech support, I have a certain natural recalcitrance to turning to the company itself for help. I presumed that I would be made to run through a litany of time-wasting tests to establish what I had already concluded. But without much in the way of recourse, I resolved to give it a shot and fired up a chat session.

To the credit of my support agent, they did ask me if I’d tried a few things, but generally accepted the answer that I had, and eventually escalated the case and scheduled a phone call with another support agent.

That second agent proved quite capable, not only agreeing that the situation was strange, but also looking into issues on Apple’s side. Which led to the somewhat bizarre conclusion of this story: after perhaps 20 minutes on the phone, he seemed to hit on something. I heard him laugh and say something along the lines of “that explains it” and then, with my consent, put me on hold. When he came back, he said—and I’m not exactly quoting, but close enough: “I’m sorry, I can’t tell you any more than this, but all your services should be back up pretty much exactly 12 hours after they went down.”

Now, in my initial forays on social media, I had gotten a reply from someone on Mastodon mentioning that Apple’s iCloud servers were sometimes put in maintenance mode for 12 hours—but upon going back and looking for that specific reply, it was nowhere to be found.

It did, however, support the theory that something had gone wrong with the particular iCloud server on which my account was located.

There was, according to this support agent, nothing to do but sit back and wait, then call back if service hadn’t returned by the 12-hour mark and reference my case number. He was again apologetic for not being able to give me any more information, but reiterated his confidence that everything would be resolved.

So I waited the rest of the day. At this point, I had received no email since the early morning, and a number of my other apps—though not all—were non-functional. It made me realize just how much of my life was dependent on Apple’s online services—a somewhat sobering proposition.

I spent the next few hours largely offline, but kept an eye on the clock. And, sure enough, at 9pm on the dot, everything flipped back on: all my Find My friends showed up, my email started slowly trickling in,¹ and I was able to finally fully log back into my iCloud account on my MacBook Air—just in time to go to bed.

We interrupt this program…

Overall, the experience was confusing and irritating. If this was a server maintenance, upgrade, or migration situation, why not simply tell me? Would it shatter the illusion of iCloud as a monolith of silently functional services? (Breaking news: that illusion was thoroughly punctured anyway.)

Moreover, if this was some kind of scheduled procedure, why not warn affected users ahead of time? The idea that my email—which I rely upon for work—and a slew of other services might be interrupted for essentially an entire workday with no notice whatsoever is technological malpractice. My cable company tells me when it’s doing work in my area and there might be service hiccups, and you can bet that the hosting provider I use for my website communicates whenever there might be something that affects my service.

The most plausible suggestion, as suggested by my co-hosts on The Rebound, was that some sort of legal compliance (such as a subpoena or national security letter, for example) might require temporarily freezing the server and not divulging that information to other users. Which does seem to tick most of the boxes, but certainly doesn’t make me feel any better. Even in that case, surely there must be a way to avoid inexplicably disrupting the critical services of many people.²

But such is the nature of black boxes. iCloud’s always been particularly bad in this regard, which is one reason I, like most tech-savvy folks of my acquaintance, would rather do something really unpleasant like cram my mouth full of radicchio before logging out of my iCloud account.³

I heard from many a person on Mastodon while I was going through this about similar issues where iCloud was disrupted for one reason or another, with little or no communication from Apple, but let me be clear: this isn’t just about the catastrophic level of interruption that I fell prey to. Low-level iCloud woes are a frequent and ongoing frustration for almost everybody who uses the service, whether it’s tiny files that refuse to finish uploading to iCloud Drive, or collaborative notes that don’t update in a timely fashion, or multiple Messages conversations that spring up with the same people—and to be clear, I’ve seen all of these. People have been wishing for a manual “sync” button for iCloud for as long as I can remember.

Even as my iCloud service has slowly returned to normal, I’ve seen some lingering issues. For example, when my MacBook Air was disconnected, it had one folder from iCloud Drive archived locally and removed from the cloud. That folder didn’t even contain all the documents it was supposed to, but I was thankfully able to go back through Time Machine and retrieve them. Elsewhere, my reminders on one device took a while to actually sync my data back. Who knows what other surprises may be lurking?

Boxed in

All of this black box ethos goes back a long time. Ten years ago, I wrote an article for Macworld about iCloud’s silent email filtering, a server-side system that’s intended to filter out spam but has occasional false positives—and more to the point, is not documented anywhere, which could mean that legitimate emails simply never arrive and you’d never know.

I was reminded of this a few months back when I got an email referencing that piece:

I ran across an article you wrote 10 years ago while searching for an issue I have today. I can’t believe that even today this is still an issue with Apple. Do they not listen? Not care? They recently opened up iCloud to use custom domains, which is how I ended up there. They seem to want to sell “email as a service”. But they don’t seem to want to operate it as a legitimate business. Sad…guess I will end up moving back to something else. 🙁

Apple talks a good game about services, elevating them to equal standing with its hardware and software. It’s put a lot of emphasis on growing the revenue of its Services division, and as with its default apps, it gets a ton of mindshare by being both integrated at a low level and free.

The thing is Apple fundamentally doesn’t want you to think they’re like “other” service companies. They’re not going to send you emails about upcoming outages, or a digest of all the spam that silently got blocked from your account so you can find the ones that should have gotten through, because it flies in the face of the image that Apple wants to put forth, that their magical system “just works.” But the problem with a black box is that once you’re inside, you have no idea what’s going on—and it’s even harder to get out.

[Dan Moren is the East Coast Bureau Chief of Six Colors. You can find him on Mastodon at @dmoren@zeppelin.flights or reach him by email at dan@sixcolors.com. His latest novel, the supernatural detective story All Souls Lost, is out now.]

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