Apple iCloud Migraines

Check the end of this post for updates. Soon after I posted this the issues popped back up. The saga continues.

Oh, Apple. You make it sound so easy. Can’t sign in with an Apple Watch? Devices having syncing problems or lose connectivity to the Continuity/Handoff magic? Sign out of iCloud and then sign back in. Problem solved? Sometimes. For a time. Not every time.

Signing in and out of iCloud to fix issues can create random headaches as nasty as a migraine. You never know when those migraines are going to hit. You live life a bit on edge anticipating and dreading the next reccurence. You know it will happen. Or you fear it will. And when it does hit, well you know what’s coming.

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I haven’t blogged about things Apple in awhile. Not since this post on Apple’s Design Trap. But it feels like my pace might pick up a bit given the frequency of new kinks I’m experiencing in the Appleverse. Funny, not funny, how these migraines seem to surface in the run up to Apple’s annual new operating system announcements at WWDC and then continue throughout the summer. It almost feels like whether we sign up for betas or not, we’re all along on the summer beta bus for the ride anyway. Especially if we take advantage of the number of services and features connected to iCloud.

Yes. iCloud. Troubled when launched, it is less, though still troubled now. But though it may be less, it’s actually become more mysterious because it’s tied to so much more than when it had its troubled beginnings. When I say mysterious I’m not just talking about how users feel. Talk to an Apple Support rep about an iCloud issue. Beyond advising signing out and signing back in they are by and large as confused by the mystery as the rest of us.

Here’s the story.

I’m a big Apple fan so I come at my criticisms of Apple from the point of view that I enjoy and prefer Apple’s devices and software. I use a variety of Apple’s computers and products. I also subscribe to iCloud via AppleOne. I like to take advantage of quite a few of the features that require an iCloud subscription to benefit from such as Sign in with Apple Watch, Universal Control, Handoff and Continuity. Prior to last fall’s release of  Ventura, iOS16, watchOS9, etc.., iCloud would somehow randomly bungle things up so these features would just stop working. Typically you don’t know that things have stopped working until you go to use one of the features. The problem(s) seemed to be resolved after the Fall 2022 releases of those new OS’s. But as we all know Apple keeps working and releasing updates throughout the year.

After this past spring’s release of Ventura 13.3 the problems appeared again. After the release of Ventura 13.3.1 I didn’t see any of these random cock-ups and dared to breathe a sigh of relief. Premature as it turns out. Even though there were mutliple device categories involved in the 13.3/16.4 round of OS updates I’m pinning this on Ventura because in attempting to track problems down I discovered that there were no issues with any of these features between iPads and iPhones. Turn off the Macs and things worked as designed. Call me crazy but “Turn off your Mac” sounds slightly worse than “you’re holding it wrong.”

Coming back to either of my Macs (MacBook Pro M2 and iMac 24) I could randomly no longer log in with my Apple Watch. That’s a first world problem I know, but hey, it’s my first world so it’s a problem for me if not for any substantial number of users. And of course the error message Apple offers is about as helpful as warm spit.

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For those that don’t know there’s no place to “sign in” using the Apple Watch app on your iPhone. To sign out of iCloud on your Apple Watch you actually have to sign out of iCloud on your iPhone and the reverse is true. So this little not so helpful message should tell you to sign out of iCloud for your iPhone. Oh, and the clever little animation in the above GIF is showing the enjoyable experience I would receive when I tried to toggle the control that lets me sign in with my Apple Watch. Top notch support and design. All around.

Once I arrived at this goodness I would then check to see if any other of the Continuity/Handoff features would be disabled and of course they would be.

Consistently Inconsistent

Now here’s the bigger problem. There’s no consistency to the failures. Sometimes the problem would be on both Macs and sometimes on one of the Macs, (it seemed like they were taking turns). Once I rebooted the MacBook Air to attempt and resurrect the lost iCloud features connection and in that case I had success. Only to see that the connection on the iMac had failed in the time it took to reboot the MacBook Air. In almost all instances there was nothing out of the ordinary added to either machine (that I’m aware of) or me using the machines in any new or different way. Other than an operating system update. (*cough*)

Prior to Ventura I had talked with Apple Support and scoured online sources for solutions when this problem would manifest. There were and are as many guesses to solve these problems as there are people looking for answers. Everything from rebooting to rebuilding your device(s). The same is true in this current moment. In some cases a reboot solves the issues. In some cases not so much.

Others solve it with any number of solutions (Bluetooth on/off, logging a user in and out, etc…). Most who get to the point of logging out of iCloud report some success, only to see the problem come back at intervals ranging from a couple of hours to several days.

Currently I’m in that latter “several days” category. It’s almost consistent at three days. Occasionally sooner. Occasionally longer. The range of unpredictability is at least narrowing. But the bottom line here is this: Apple has no idea how to solve this issue.

So there’s a problem. I can only conclude that it’s related to iCloud and something introduced recently in Ventura that affects Macs given that everything seems to work when the Macs are turned off. Signing out and back in to iCloud will solve it. For awhile. That’s the current state of affairs.

What Apple and those who leap to the “Sign out of iCloud” as a solution to this migraine-like nightmare don’t tell you is the potential series of after shocks you’ll encounter along the way back.

Apple does provide a handy list of the services you’ll lose access to when you sign out of iCloud at this link. And when you decide to take that step Apple will also let you know that you’ll lose any credit cards you have set up with Apple Pay. Apple will also give you the option to save some iCloud data on your Mac. But that advice doesn’t cover what you may or may not have to do to get things back up and running the way you want it to. These are some of my experiences:

Things that happen each time I’ve logged out and back in to iCloud.

First, if you happen to use different Apple IDs for purchases/music and iCloud you’ll have to manually reassociate your purchases/music ID with your iCloud account in the same way you do when you set up a new device. I know I’m not the only old geezer who first got an Apple ID back in the day when I used iTunes and an iPod with Windows, so I’m sure others will have to do this as well.

Second, if you use iCloud Photos and have chosen to save originals to your Mac, you’ll have to make that selection again in the settings for Photos. If you do have to reselect this Photos setting that means you’ll burn bandwidth downloading those originals again at some point.

Third, if you’ve downloaded some music to your device you’ll have to redownload those selections again. Again, Apple doesn’t seem to remember what you’ve downloaded previously.

Fourth, As expected all of your Mail, Notes, Reminders, Calendars, and Contacts have to be redownloaded. (More on Contacts in a bit.) This seems to work relatively quickly with the exception of Mail, Notes, and Contacts which can take some time depending on what you’ve accumulated.

Fifth: Apple does warn you that you’ll lose credit cards in Apple Pay. So you know that going in. Having to go through this process so frequently in recent weeks unfortunately flagged my account at my bank necessitating a phone call to explain what was going on. So I’m not re-adding that card back to Apple Pay until or if this problem settles down.

Things that happen sometimes and sometimes not when I logged out and back into iCloud.

Messages: I’ve got several group threads I hide notifications from. I sometimes have to “re-hide” those notifcations. Sometimes not.

Airpods and Bluetooth: I don’t choose the default Airpod setting that allows Airpods to connect to a Mac automatically. I use the “When last connected to this Mac” setting. That setting sometimes holds and sometimes does not.

The image I use for my avatar on my login screen sometimes comes back as normal. Sometimes not.

Contacts: I mentioned that earlier. On some, not all, occasions Sign Out/Sign In Contacts seems to want to rebuild it’s database completely. I only noticed this after one of these episodes when for the first time my M2 MacBook Air got hot to the touch. In trying to figure out the problem I noticed that the AddressBookSourceSync was the culprit eating tons of memory and processor time. Again, this didn’t happen each time, but it did happen multiple times on each Mac. Note: I hardly ever use the Contacts app on my Macs. Typically any contact I add or change comes from my iPhone.

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Various other settings and preferences seem to come and go. But again, it’s not like I use everything on my Macs every day so who knows when in this cycle of logging out and back in something changed or didn’t.

I get the problem here. Apple has created quite an intricate and appealing series of services that rely on iCloud as a backbone. When things work they work great. But they don’t always just work. Advancing these services and features requires constant development and there’s no real way to make sure every possible detail and permutation is locked down and working on the annual pace that Apple rolls out these operating systems. So, there will be problems. Bugs. Issues. Headaches. Call them what you will. Fix them and move on.

But, if things are moving so fast that your support personnel and documentation can’t keep up then it might be time to re-evaluate the pace. The misleading “fix” in that message in the animated GIF above has been around for at least two generations of Apple operating systems. Frankly at this point, it’s insulting.

iCloud woes date back to its inception. I doubt they will ever truly be solved. But at least give users and your support personnel information that makes sense, explains what your fix may or may not do, and isn’t misleading or sounds ignorant.

Updates: A few hours after posting this the issue happened again after being away from the iMac 24 for a few hours. Nothing going on just the computer normally going into Sleep Mode. As had happened once before, all was working on the MacBook Air until I rebooted the iMac. And then the MacBook Air took the same iCloud dive.

The reboot of the iMac 24 was successful and brought things back on that device. I’ve rebooted the MacBook Air 4 times now and still no luck on that device. That typically means I’ll have to sign out and back in to iCloud. I’ll update again after doing that.

Update 2: Wednesday. I logged out and back into iCloud last night. After the requisite time of letting things settle back in most things that I checked seemed to be working again. Until they didn’t. This morning I tried to open MacBook Air while having coffee and none of the features were working again. So far everything at the moment seems viable on the iMac 24.

Two more reboots of the MacBook Air seemed to right the ship.

Update 3: Thursday. Ran some errands for a few hours today. Returned. Neither Mac would accept Login With Apple Watch and all of the attendant other problems. Rebooting both machines yielded a return of things to the MacBook Air but not the iMac 24.

This is getting old.

*For a variety of reasons this post has been in the creation process over a couple of weeks. During that time the issues I discuss occured mutliple time on both Macs. I anticipate they will continue.

Author: Warner Crocker

I stumble through life as a theatre director and playwright as well as a gadget geek...commenting along the way. Every day I learn something new is a good day, so I share what I find exciting, new, stupid and often worthwhile.

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