Relief. At last. All it took was the right doctor.
We’ve all been there with health situations. You lay out your symptoms and whatever checklist your medical professional follows leads to a course of treatment that might or might not work. Perhaps after repeated tests and possible cures you might finally get the attention of someone who actually listens, goes beyond the symptom check list, and you get treatment that works to solve your problem.
If your situation and symptoms don’t fit those of the majority of patients it can be an exhausting, frustrating, and dehumanizing experience.
The same is sadly true with technical support. You have a problem. You call or chat (hopefully with a human). Lay out your symptoms and you get served up solutions from a playbook that don’t solve your problem. Striking out on your own you search the Internet for solutions, (increasingly a frustrating and useless experience), only to discover others facing the same issues.
At least you find comfort in knowing you’re not alone. Even so, there’s not enough strength in numbers if you and your compatriots fall into that ever popular yet corporately dismissed category of a “small minority of users.”
Like with your medical condition, if your technical issue falls outside of the range that most experience, then you better hope that you are talking to someone who actually listens and isn’t just a part of a solution mill that rewards quick dispensing of the call the way restaurants hope for quick table turnovers.
The Diagnosis
Perhaps you’ve read my previous chronicles discussing the Apple iCloud Migraines. I’ve been suffering with these headaches for a number of years and through a tourist guide map of California named macOS operating systems. I won’t go into detail, but you can find links to them here, here, here, here, and here. I will offer a brief summary (non AI generated) of the problem :
At each point that Apple released an operating system update, whether beta or final release, my Macs would mysteriously lose all Continuity based or related features. Continuity is the system Apple uses to connect its devices allowing users to copy and paste between them, sign in to Macs with an Apple Watch, display iPhone widgets on a Mac Screen, and connect Macs and iPads together via Universal Control. Your iCloud account is a key to Continuity.
Note that I haven’t been on a beta since owning any of my current devices. So, in theory, none of these beta updates should have affected me. However, I might as well have been downloading betas like a beta junkie, given the return of these migraines with each beta release and subsequent full releases.
Communications over the years with Apple Support yielded nothing that would help until Dan Moren of Six Colors posted about a similar issue he was facing and the responses he got from Apple Support.
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.
After Dan’s post turned the heat up a bit on the issue my calls with Apple Support changed in tone and substance. I got moved a couple of rungs up the ladder to an advanced support level. (Draw your own conclusions). Initially that seemed promising. I also got the “just wait it out” response as Dan.
Suffice it to say that eventually yielded no real solution and there were two periods of time when things just seemed to stall. The first being prior to the Apple Vision Pro release and the second in the run-up to WWDC 2024. I chalked those up to resource allocations.
Reaching the Right Doctor
Following WWDC I decided on one frustrating evening to drop an email to Craig Federighi, Apple’s honcho on all things software. I didn’t expect any response. My previous emails to Tim Cook were met with a brush off.
In the context of my email I appealed to Craig quite explicitly that I was very interested in the new iPhone Mirroring feature coming in Sequoia that relied on Continuity and how he had discussed Continuity during the WWDC presentation. I also expressed that I imagined this feature would be at best a hit and miss for me given the ongoing migraines.
Lo and behold, I got a response from Federighi requesting I share diagnostic files with him. Note I don’t know if I was actually communicating with him directly or one of his staff, but after submitting another round of diagnostic files I received the emails below:
And then I received the following:
Once macOS Sonoma 14.6 and iOS 17.6 were released the problem did indeed appear to be solved, but I knew I would have to wait through the next few beta releases and also the release of Sequoia to determine if the fix would indeed hold.
The good news is that I can report the fix did indeed hold through the remainder of the beta cycle and also through the final releases of macOS Sequoia 15 and iOS 18. As of today it has held through developer betas and also public release of the betas for 15.1 and 18.1 since installing the final versions of macOS 15 and iOS 18 the day of their release. It has also held through upgrading my iPhone and Apple Watch.
I’m glad this seems to be resolved but I’m going to remain skeptical until we see the .ox and .x releases of Sequoia and iOS 18 roll out. To be honest, it feels like I’m waiting for any sign of a possible reoccurrence of a medical symptom.
Wrapping Up
I’ve always tied my migraines to problems somehow related to my iCloud account and it appears those suspicions were by and large correct. I don’t have a definitive answer but given that only a “small percentage of users” experienced this issue combined with comments from support personnel and a few clues from Dan Moren’s post, that is what logically makes the most sense to me and a few others I’ve consulted, social network buddy Dwight Silverman among them. By the way Dwight led me to a workaround involving signing out and back in to Messages in iCloud.
I’m certainly appreciative of Craig Federighi or his office pushing this forward to a resolution. I’m reasonably convinced it helped that iPhone Mirroring, which relies on Continuity, is one of the sexy tent pole features of this year’s new releases finally probably brought quicker attention to the issue. That and a stroke of good luck with my timing.
Unfortunately, for whatever reason, users in situations that don’t have a large podcast or online audience and can’t stir up a major hullabaloo in the tech press are left to piece these clues together. Unless on a rare occasion they catch the attention of a higher up at Apple to find a resolution. That shouldn’t be the case.
Certainly the bigger a company becomes it’s easier for all sorts of issues for a “small minority of users” to fall through the cracks and for priorities to shift. That’s just a reality. And it shouldn’t take the luck of good timing in sending an email to a top executive, certainly busy with many other tasks, to suss out an issue.
As I’ve said all along, Apple needs to find a way to come clean with both users and its front line support personnel when these issue present themselves. Listening should be the key because sometimes the patient/user has all the clues you need to help them.
You can find more of my writings on a variety of topics on Medium at this link, including in the publications Ellemeno and Rome. I can also be found on social media under my name as above.
https://warnercrocker.com/2024/09/24/at-last-a-cure-for-apple-icloud-migraines-thanks-to-craig-federighi/
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