technology – Page 8 – Life on the Wicked Stage: Act 3

A WWDC 2024 Reading List

A reading list of predictions and commentary heading into WWDC 2024.

There are always lots of predictions about what Apple will announce at its annual World Wide Developer’s Conference each year and this year is no different. I’ve written a few of them myself. Here’s a quick list of some pieces from others and myself that I think provide a good pre-WWDC reading list.

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Mark Gurman of Bloomberg seems to have gotten quite a few of the details, whether leaked or planted who really knows, on what’s about to unfold. Check out Here’s Everything Apple Plans to Show at It’s AI-Focused WWDC Event. It almost feels like a story board of the event.

Gurman also expands on his thoughts about Apple Intelligence here.

As a companion to that check out John Gruber’s take on Gurman’s Epic Pre-WWDC Leak Report. Gruber seems to think it’s indeed a leak and the folks inside Apple aren’t too happy. IYKYK

Perhaps the best pre-WWDC piece for providing some pre-perspective comes from Om Malik in Apple + AI: What to Expect at WWDC 2024.

Wayne Dixon tackles his Wish List by platform and tosses in a Bluetooth wish for good measure.

David Lewis doesn’t think we should hold our breath.

Since Artificial Intelligence, or as it appears soon to be christened Apple Intelligence, seems to be the order of the day, Craig Grannell has some intriguing thoughts on how Apple can avoid the pitfalls others have made in this great AI gold rush.

Nathan Edwards at The Verge wants to know if WWDC 2024 and AI will unlock the potential of the iPad Pro.

And here are the three pieces I’ve written:

WWDC 2024: iCloudy Forecasts Ahead Amidst Dampening Expectations

WWDC 2024: Apple Needs To Do Some Serious Work with iCloud

WWDC 2024: Things I’d Like To See

It’s always interesting to see what comes out of each year’s WWDC announcements because one way or the other they set much of the agenda for the next year and beyond.

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.

WWDC 2024: Things I’d Like To See

Bring in the new and shiny, but fix the old and buggy too.

The Internet is filled with wish lists of things Apple fans would like to see announced next week at WWDC. New things. New capabilities. New all round. The majority of those wishes are the same and focus ahead. Nothing wrong with that. We’re always advancing. Or so we’re told.

Perhaps I’m stuck in the past, but I’d rather see Apple devote time to correcting some longstanding issues that bug me. Many of these issues are part of the glue that holds Apple’s ecosystem together, or what Apple calls iCloud and I call the unnamed operating system, iCloudOS. So, I’ve compiled a list of things I’d like Apple to fix, repair, or at least pay some real attention to.

Chances are better than good that you won’t hear much about any of this next week or in the weeks that follow. Many of these issues have existed for a few years now and seem to be such a low priority that Apple must be content to let them exist. Quite a bit of this could be considered small in comparison to the bigger challenges brought on by adding new features that bring new complexity. But one of the reasons so many prefer Apple’s way of doing things is the attention to detail in both design and practical matters. When it’s good it’s great and often magical. When Apple loses focus and doesn’t pay attention it can be like watching a magician pull a dead rabbit out of a hat.

For me these issues are rough enough and present enough inconsistency to diminish that attention to detail. The longer they are ignored or put off the more they point to glaring weaknesses in Apple’s process and I think we get farther away from that “magical” or “it just works” lore.

It’s apparent that not enough others feel the same or have the same experiences to pressure Apple into devoting the resources necessary to address these annoyances. That’s not a surprise. New always takes precedence in a market driven by delivering something new each year. And AI is the big new thing this year and Apple has assigned all hands on deck to ready what most expect to be the newly christened Apple Intelligence ship to sail.

Yes, we’ll hear quite a bit about AI. I’m also sure we’ll hear about things like emoji, flashy Messages and other novelties that show well in demos. Many of those I consider trivial or “meh” features that will be forgotten shortly after all of the reviews are written. Though the money I spend on Apple products is a small drop in Apple’s buckets of cash, I’d much rather see it spent putting resources into fixes for these annoyances. The list below certainly isn’t a complete one, but these are the things I’d love to see Apple address.

WWDC 2024: Apple Needs To Do Some Serious Work With iCloud

iCloud OS: Apple’s Unnamed Operating System. The second in a series heading into Apple’s WWDC 2024.

WWDC is designed to highlight future directions for Apple’s increasing number of operating systems and how they work together. The OS list is long and getting longer, but there’s actually one that Apple has never mentioned as an operating system, yet it’s the one that glues every other piece of the ecosystem together. I call it iCloudOS. Like any glue it can fasten and bind, but apply it without care and you can end up with a sticky mess. iCloudOS is a bit of both.

If you use multiple Apple devices iCloud ties them all together creating a supposedly fluid connection between devices and services. That’s the attraction of the ecosystem. When it works as designed it can feel magical. Copy and paste between devices, universal control, handoff, shared Notes and Reminders and others all make Apple computing life more productive and often more fun.

When things don’t work it reminds every parent of raising a child. There are moments of sheer wonder and joy, but you know at some point the kid is going to shit the bed. There’s too much of the latter to ignore.

I’ve written extensively about my iCloud woes (here, here, here, here, and here). I’ve had numerous conversations with Apple tech support personnel. What I’ve discovered is that there are ongoing iCloud backend issues that Apple hasn’t been able to solve. They keep trying, but they keep getting put on the back burner once Apple gears up to roll out its next big new thing, as is the case with this year’s now well predicted AI announcement. Things reach a point when a “wait until next year” mandate takes hold that would test even a Chicago Cubs fan’s patience.

In my most recent adventures into the backend of iCloudOS it has been acknowledged that all of the work we were doing to pin down the issues I and others have been seeing has been put on hold until after whatever is coming next in the various operating systems due to be announced next week. All well and good, I suppose, but here’s the problem with that. That approach essentially makes all users of the ecosystem beta testers. I do not run betas on my devices but I’ll suffer through the numerous summer releases and whatever changes Apple makes on the backend during the summer beta season. That will continue with each point release throughout the year. Keep in mind, we’re all, always at the mercy of the backend.

I’ve already seen this begin to happen and the betas don’t roll out for a week or so yet. One of the early warning signs(and there are quite a few) that things are happening in iCloudOS is when notifications for Apple’s Reminders app get out of sync between my macOS devices and iOS devices.

WWDC 2024: iCloudy Forecasts Ahead Amidst Dampening Expectations

iCloudy Forecast Ahead for Apple at WWDC

Here it comes. Apple is heading into its annual World Wide Developer’s Conference (WWDC) with announcements of its next big things beginning June 10th. By all accounts, this year those next big things will center on AI which is short for Artificial Intelligence. There won’t be any shortage of AI in a tech world that has grown both AI crazy and AI fearful, putting Apple is in the unusual position of playing follow the leader in more obvious ways than in the past.

There will be other new features announced for iPhones, Macs, Apple Watches, perhaps even the Vision Pro, but as always the focus will be on what’s new. Even though a goodly portion of what’s new and exciting each year often ends up being a bit “meh” in the end. Either “meh” or rolled out and forgotten as Apple shifts its attention to what next year’s next big things will be. That seems to be what’s happening this year as Apple has turned most of its focus to AI.

Apple is also unfortunately positioned to have to work harder in making its splashy announcements splashy and dodging seemingly already diminished expectations on a number of fronts. Most anticipate Apple’s AI announcements to be less than sexy and the iPad faithful/hopeful seemed to be poised to continue piling on the criticism (some necessary, some not) that greeted newer iPads less than a month ago.

So, on two big fronts, AI and iPadOS, Apple has some tougher challenges ahead than it usually does this time of year. And bad timing is at the root of both.

The iPad Issue Is Touchy

On the iPad front, for whatever reason Apple went more than a year before releasing new iPads. When they did debut them last month they surprised everyone by including new M4 chips in the new Pro lineup, upsetting every pundit’s attempts at trying to assign a predictable timetable to the continued Apple Silicon evolution. Coming just weeks ahead of WWDC, and without any new operating system software to accompany it, Apple opened up a slew of doors for the salivating pundit class to rush through, cranking up the complaints about iPadOS not taking advantage of very powerful and much loved hardware. And, as always, the married at the hip debates about being able to run macOS on an iPad or adding a touch screen to the Mac tagged along as noisy bridesmaids.

It’s a bit frustrating for a regular and religious iPad user. While the issues are genuine, they negatively dominate the conversation given that they come from the influential voices that helped turn the iPad into a success in the first place. I know the issues are long simmering, well intentioned, and come from the heart of those who love the device, but the recent sudden crescendo was deafening enough to fire up a Loud Environment warning on an Apple Watch. With WWDC just around the corner everyone knew the new devices alone were not going to offer anything remotely close to a new and different iPad experience. It just seemed premature to me. If they were meant as a warning to Apple, then I would call it not only premature, but a misfire given the timing.

Those debates and complaints probably aren’t going to end in the foreseeable future as entertaining and exhausting as they can be. Between manifestos, and well thought through lists of what some desire on iPads, there was some general vitriolic piling on. It heralds a tough year ahead for Apple and its iPad lineup.

My prediction is that no one is going to be remotely satisfied with this year’s iPadOS release. Most rumors say not much of consequence will be announced. It’s certainly going to be interesting to follow the commentariat class as they wrestle with how many different ways they can say the iPads are great devices but Apple keeps holding them back for another year.

Perhaps this year changes things, but typically big OS changes come to the iPhone first with iPads and Macs bringing up the rear in the year or years that follow. Given Apple’s push into AI as this year’s big iPhone tent pole, if the iPad doesn’t get included it will add even more to those complaints and increase the volume.

Sunday Morning Reading

Secret octopi, culture wars, convictions, and reading between the letters. In this week’s Sunday Morning Reading.

Life is beginning to settle in after the big move, although there’s parts of it we still can’t figure out which box we packed some of it in. Perhaps we need some sort of A.I. bot to help us figure that out. But we’ll get there. In the meantime here’s some Sunday Morning Reading to share.

Speaking of AI, WTF is AI? That’s the question posed with some attempted answers by Devin Coldeway. It’s a decent primer on the topic. Watch out for secret ocotopi.

A couple of pieces on AI from Nico Grant at the NY Times shows just how unknown and perhaps reliably unreliable this fast evolving tech territory is. First up is Google’s A.I. Search Leaves Publishers Scrambling. Follow that up with Google Rolls Back A.I. Search Feature After Flubs and Flaws. I wonder how AI will spit all of this back at us once articles like these are trained in. I also wonder when publishers will start to standardize whether or not we’ll write it as AI or A.I.

Some think The AI Revolution Is Already Losing Steam. I happened to agree with Christopher Mims, the author of this piece.

Even in the midst of moving it’s been tough to ignore the political comings, goings and convictions in the news. Check out David Todd MCCarty on Bedtime for Bonzo, Or Nothing To See Here. Even after 34 convictions for the orange dude, this piece holds up.

This piece from July of 2021 by John Pavlovitz resurfaced in my feeds in the last week. The Sadness of Sharing A Country With Trump Supporters is worth a re-read in the wake of this week’s news. Somehow I think it will remain relevant for quite some time.

With all that is going on in the political world, it’s a good idea to always remember there is so much more going on behind the scenes than we ever want to realize. Check out Ken Silverstein’s look behind the curtain in Off Leash: Inside The Secret, Global, Far-Right Group Chat. You might be sorry you did.

I hope The Wonkette is writing you visit often. There’s an excellent serial novel there called The Split by Ellis Weiner and Steve Radlauer. It’s up to Chapter 30. It’s terrific and worth your time.

There’s a new book worth highlighting and highlighted by Laura Colliins-Hughes in the NY Times. James Shapiro’s The Playbook chronicles the history of The Federal Theatre Project. The subtitle teases well: A Story of Theatre, Democracy and The Making Of A Culture War. A great story from back in the day when live theatre was actually something folks believed was dangerous enough that it could change minds.

And to close out this week’s edition check out Natasha MH’s Writing The Unpretentious Prose. Don’t just read the words. Look between the letters.

If you’re interested in just what the heck Sunday Morning Reading is all about you can read more about the origins of Sunday Morning Reading here. You can also find more of my writings on Medium at this link, including in the publications Ellemeno and Rome.

The iPad Pro Ad Apple Should Have Released In The First Place

Less Crushing. More Creative Fun.

Just before this year’s World Wide Developer Conference debuts Apple has released a new ad for the iPad Pro. It’s probably the one it should have released in the first place, instead of the now infamous Crushed ad. It’s better than the previous ad in a lot of respects. Certainly it better shows off the iPad Pro’s capabilities, but I’m not sure it’ll ever erase the crushing response from that first ad. CleanShot 2024-06-01 at 07.53.37@2x.

You’ll remember that furor visited on Apple after releasing Crushed featuring all sorts of musical instruments and other creative tools being crushed by a hydraulic press into an iPad Pro. I for one wasn’t that upset about the ad, but quite a few folks thought Apple misread all sorts of rooms and moments. Given how the creative classes are a bit squeamish about AI possibly replacing artists and crushing the human element out of the act of creation it lit a spark that eventually led to a rare Apple apology.

This new ad shows off what the new iPad Pro’s can do featuring three different artists creating three different backgrounds while actress Sofia Wylie dances around in front of a green screen. Even the Apple Pencil gets some screen time.

Here’s the new ad called Worlds Made on iPad. Better to make than crush.

You can find more of my writings on a variety of topics on Medium at this link, including in the publications Ellemeno and Rome.

But the Demos Aren’t Lying

Steven Levy has seen enough AI demos to think we should believe the hype. I’m still in wait and see mode.

Call me curious. Call me skeptical. Two sides of the same coin. The tech industry is dancing on the edge of a coin called Artificial Intelligence waiting to see which side lands face up. As they dance, we also dance, because the promise/hope/hype/hyperbole is that the technology will make lives better, fill lots of coffers, and set us all free (except for that sure to increase every year subscription price) to enjoy more of life.

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Steven Levy has apparently seen enough demos that he has penned a piece telling us that It’s Time to Believe the AI Hype. It’s a well reasoned piece, as usual from Levy, and worth a read if you’re trying to follow what all of this means. But the moment that caught me was this quote:

Skeptics might try to claim that this is an industry-wide delusion, fueled by the prospect of massive profits. But the demos aren’t lying.

“But the demos aren’t lying.” They may not be. It all might come true. Or some of it. Or enough of it to matter. Even so, I’ve been around enough blocks too many times to stake anything on any demo for any product. Some do pan out. Too many do not. Given the pace of things in tech these days, I’m guessing that once the inevitable explosion yields to the equally inevitable contraction, there’s a better than average chance that we’ll be eyeing some other piece of universe altering tech within a year or two.

The reality is what’s coming in AI is coming. We’ll all get a taste. The proof wil be in how we digest whatever tech related nutrional value it offers.

You can find more of my writings on a variety of topics on Medium at this link, including in the publications Ellemeno and Rome.

Thoughts on Thoughts About New iPad Pros

Let iPads be iPads. Trying to be all things to all people doesn’t work in life, and I don’t think it works in tech.

Years ago when I was a Microsoft MVP for Tablet PCs I attended an MVP Summit in Redmond. It was an exciting and stresssful moment for Tablet PC advocates, of which I was one. The winds of change were kicking up and hinting that Microsoft would favor Touch over pen based Tablet PCs in the future. For broader context, the PC Pundit industry had already declared the Tablet PC a largely failed niche device.

Then Microsoft CEO Steve Ballmer was to give the keynote and take questions from the audience. As I lined up to ask a question I noticed that he was taking notes on a piece of legal paper. I never got a chance to ask my question which is probably a good thing because I changed what I had prepared to ask. Had I gotten the chance I was going to ask why he wasn’t using a Tablet PC to take notes. It certainly would have made a big statement if he had done so. It certainly did make one that he didn’t.

Preparing to watch Apple’s recent Let Loose announcement about new iPads I was reminded of that moment in watching the usual, now almost cliché, iPad criticism flow through my social media timelines. There are two routinely rhetorical responses about the iPad:

The iPad lineup is confusing.
The iPad Pro needs to be more Mac like and/or run macOS.

Each of the above is true. Clichés are rooted in variants of truth. Yes, there is confusion, but on the first point I think Apple largely let loose the air out of a that balloon.

There’s now an easy roadmap to follow if you’re interested in a full-sized iPad. $349 will get you an iPad without many of the bells and whistles, perfect for a child or a mother-in-law. You can spend upwards of $3000 for the fully kitted out iPad Pro. Or you can settle in the middle for a $700 starting point for the iPad Air that now includes most of the technology previously only seen in the iPad Pro lineup. That all makes good sense to me. Oh, and the iPad mini is still around and I’m guessing we’ll see an update of that later this fall.

Apple is largely to blame for the second confusion point, due to a rare misfire in its marketing years ago. Before we had Apple Silicon in MacBooks things weren’t looking great for the MacBook. There was lots of talk about the iPad being the future and what it would take to make it so. Apple even launched a What’s a Computer? campaign in 2017 promoting iPads that helped confused the issue.

Tech pundits took their cue. They pushed the envelope on their devices and pushed Apple to keep on keeping on and the iPad Pro (introduced in 2015) kept getting more powerful and more capable right along side the “The iPad is the only computer I need but it needs more” stories. But hardware is only part of the story.

Things continued to get confusing when Apple split the iOS operating system into two and birthed iPadOS in 2019. Certainly that hinted at more to come from the software. Even so, the software narrative continued to feel incomplete while the parallel story of the immediate success of Apple Silicon Macs intensified the dissatisfaction.

Now, let me be clear. I’m not one of those who feels the iPad needs to be more Mac like or run macOS. Could there be advancements to iOS? Yes. I’d love the File system to work more intuitively. Quite frankly, I’m fine with how iPads sort of multi-task now, Stage Manager being the exception.

I use an iPad Pro with a keyboard at times, but I mostly use it as a tablet in landscape mode for work with an Apple Pencil. I’m a use the right tool for the job kind of guy when it comes to tech. Since both Microsoft and I abandoned Tablet PCS, an iPad has always been the right tool for most of my work in the theatre, alongside a Mac for portions of that and other work. I don’t see that changing, given that I’ve tried most of the other tablet options out there. Let iPads be iPads and Macs be Macs. Trying to be all things to all people doesn’t work in life, and I don’t think it works in tech.

In my view, the “iPadOS isn’t complete until it can be a Mac software” story has created a myth like reverse branding similar to the negative one of Microsoft’s Tablet PC. So much so at this point, I don’t think Apple will ever be able to counteract it, even if it did create an iPadOS that runs macOS or some version of it. And that’s a damn shame.

I made this comment prior to the Let Loose event, yesterday.

I could very easily be wrong, but I don’t think we’ll ever see that mythical iPad that some wish for. Personally I don’t think it’s necessary and I’d be more than happy if we just let iPads be iPads and Macs be Macs. We’ll see how and if the story changes at WWDC in a few weeks. I’m guessing it won’t and I’m just fine with that.

You can find more of my writings on a variety of topics on Medium at this link, including in the publications Ellemeno and Rome.

What Happens to Ads with AI Summaries of Web Pages?

Will AI summarize web ads into submission?

Artificial Intelligence is still the dominate tech craze of the moment. Big announcements are expected within the next several weeks from Apple, Google and just about anyone else who can prompt an AI generated press release into being. I’m sure AI will continue to be on the tips of most digital tongues.

Or will it all just be summarized?

One of the trends I’m seeing predicted is how users will take advantage of Artificial Intelligence to summarize web pages. That sounds like a useful, perhaps noble idea but it raises questions. The web relies so much on advertising to generate revenue. AI is supposed to help ad creators and marketers do better and more efficient designing and targeting. What happens when users stop visiting web pages and just rely on summaries? That’s a genuine question I have and would love to read some possible answers.

It’s not that I’m a big fan of ads, but I remember back in the heyday of RSS that there was all sorts of tension regarding losing ad impressions between web publishers and web users that relied on RSS readers. Then RSS feeds of web articles got truncated into teasers to send users clicking. Then ads got inserted into RSS. Will the same thing happen with ads being inserted into AI summaries? How would that work with something like an AI Pin or the Rabbit R1? (Although I doubt those devices will be around for us to find out.)

Given that one of the other predicted AI trends is being able to verbally converse with whatever AI machine you choose, how would that work with advertising? Will a user need to listen to ads before getting a response to their prompt? There’s already a lag in compute capacity resulting in delays delivering responses to queries with most current AI engines. I don’t imagine waiting for an ad insertion will help improve on that.

Again, these are sincere questions that I’d love to hear some thoughts on. Just don’t summarize 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.

Time for Apple To Come Clean About iCloud: Part 2

It’s been a week and Apple needs to tell users what happened on April 27 when so many had to change their passwords causing confusion

Last week, beginning on Friday April 27, quite a few Apple users experienced a disturbance in the force when all of sudden they were prompted to relog into their Apple ID on their devices. On attempting to do so many discovered their accounts were locked for “security reasons” and needed to change their passwords in order to get back in. Eventually the situation righted itself as everyone eventually was allowed to change their passwords (there’s more to that part of the story later). It’s been a week and Apple has yet to publicly comment on what caused the issue. That’s a problem.

Apple and other companies spend enormous resources to keep users and systems safe, guarding against privacy attacks and security hacks. Apple also spends mountains of marketing money touting its approach to security and privacy as a key selling point. All that’s well and good. We live in an age of online paranoia when every security alert, every email, every text, every phone call, every link we are prompted to click on is suspect. Apple Security Notifications are now in that list.

When folks started receiving prompts on their Apple devices to change their passwords and then discovering that they were locked out of their devices, that paranoia rippled across the Internet as social networks, forums, and support networks burbled with users wondering if this was a hack, a glitch on Apple’s end, or just another run of the mill online inconvenience. Depending on which Apple Support rep you got on the phone you were told there wasn’t a problem or helped to relog back in. The event was blamed on all sorts of culprits from foreign countries to AT&T after its recently revealed compromise. There was no messaging from Apple. There’s been none since.

There are some signs that it might have been a system update on Apple’s end. Gone wrong or right no one knows. Was Apple hacked and did it pull a maneuver to protect users? Was Apple attempting to update or perform system maintanence? No one knows. No one knows still.

John Gruber on Daring Fireball pointed to Apple’s Developer System Status dashboard that showed maintenance scheduled for that Friday evening and another scheduled for the next day under “Account.” So that may be a possibility. Without any communication from Apple users are left in the dark.

In my opinion most likely this incident may have been related to a backend maintainence issue. Yes, that’s a speculative opinion, but it’s based on my long (too long) experience trying to sort out ongoing iCloud failures with Apple Support. My personal conclusion is that Apple has problems with its backend operations that it either can’t figure out or is unwlling to devote enough resources to fix in a timely manner before it cycles into finishing up the next OS release.

Before I get to that, and what I experienced on April 27, let me just say that Apple (hell all companies because every company is online and subject to hacks) owe users open communication at the very least. Equally as important, Apple owes its own tech support personnel open and better communication on these problems. That’s the reason for the Part 2 in the title of this post. Apple not only refuses to give users accurate information, but does the same with its own tech support personnel. It’s been an ongoing issue and in the wake of this latest situation apparently extends far beyond the typically convenient and meaningless excuse that only “a small percentage of users were affected.” The events of April 27 may not have affected all users, but this time there was more than a “small percentage.”

Selfishly, as the evening unfolded and things started to feel very familiar, I actually hoped that the larger number of users reporting complaints might actually lead to some communication that could possibly help resolve my ongoing issues. But so far that’s not the case.

Friday Night’s Apple ID Fracas

My wife and I were watching an episode of Palm Royale on Apple TV+ via an Apple TV. A message popped up on the screen saying I needed to update my Apple ID password. I thought this was strange as I never recall having to enter my Apple ID password on an Apple TV before. Typically with my iPhone nearby signing in just “magically” happened.

I grabbed my iPhone and noticed the same message there and then the Apple ID Locked message appeared. My first thought, like so many others, was that I had been hacked or there was an issue on Apple’s end. I went to my iMac and fired up social media apps and also headed to Apple’s System Status webpage. Nothing helpful there, which isn’t surprising. But on social media I started seeing the typical “Is this happening to anyone else or is it just me?” posts start to scroll through my feeds. Chance Miller at 9to5 Mac was the first publication to report on the issue.

I then got the same notification on my iMac which cascaded to my other Apple devices. As the event unfolded I experienced a very similar series of events as told by Michael Tasi in his excellent blog post Janky Apple ID Security. There were some differences. Bottom line: I just couldn’t log back in after several attempts to change my password on my iPhone.

Logging in with a new password would fail, spinners would spin, and prompts would overlay causing a guessing game as to which button to push. At one point I got the following screen on my iMac.

It’s curious. The date I’m publishing this post is May 3 and as you can see above there’s supposedly a new device on my account that can’t be used to edit my information until May 3, 2024. Which device? Who knows? I’ve had use of all of my devices since I successfully relogged them back in with the new password on April 27 and I’ve since edited account details from the iMac, which I assume is the device in question since that’s were the notification popped up. But who knows?

At one point while attempting to change the password on my MacBook Air I was asked to enter the device password for my iPad mini. Again that’s curious. I had not yet attempted to change the password on that device or even attempted to wake it up.

After successfully changing my iCloud password and relogging back in to my iPhone, iPads and Macs, I was still unable to do so with my Apple TV and Apple Watch until I manually entered the new password on each device. Again, I’ve never previously had to enter an iCloud password on either device. Also curious, as of this writing I no longer am able to control my Apple TV with my iPhone or Apple Watch. Is that the mysterious “until May 3” device? So far that hasn’t resolved if it is.

The “Not” Fun and Games Didn’t Stop on Friday Night

After feeling relatively confident that my passwords on each device had been changed succesfully we finished watching the episode for Palm Royale and retired for the night. Note that my wife’s iPhone and iPad did not experience any of these issues. Neither did other family members I support.

The next morning I discovered that I had more to do in order to bring my devices back up to full speed. First, I had to relog in to Messages on each of my devices. I also discovered that all my App Speciifc Passwords had been deleted, which of course required creating new ones. To be honest, I’m not sure I’ve done so with all of the apps that require them yet because all of the passwords were erased. I can’t remember which apps required them and which ones didn’t. Those I use frequently, such as Fantastical, let me know right away. I assume I’ll hear from the others as they rotate back into usage.

After searching social media and other sites I began to notice that users who had fallen prey to whatever this was experienced a range of issues, but not all of the same issues I did. Some experienced more and different ones. Those running HomeKit and HomePods (I don’t) had their own set of different issues. Folks were confused and waiting for an answer.

One of the confusing discoveries is how Stolen Device Protection is supposed to work. Supposedly if you’re in a “Familiar Location” you don’t have to endure the waiting period unless you set up the system to require it at all times. But others, searching Settings for “Familiar” or “Significant” Locations, (Settings/Privacy&Security/Location Services/System Services/Significant Locations) discovered that their “Familiar” home or work locations were recorded outside of the radius for it to be “trusted” leading to the one hour delay.

Tying This Incident to Ongoing Issues

I won’t go into a blow by blow account with my iCloud Migraine issues. You can find those specifics in blog posts here, here, here, and here. That said, having to re-log into Messages after this event leads me to continue to believe that Apple has deeply rooted issues with iCloud. I’ve been fighting these issues (and Apple) for well over a year. Within the last five months or so a workaround that Dwight Silverman clued me into has been a way to get the ship righted in most instances when they reoccur.

Briefly, when I lose Universal Control, Sign in with Apple Watch, Handoff, Copy and Paste between devices, the fix is to sign out of Messages in iCloud and to sign back in. When these fuctions disappear from my Macs they are still available on iOS devices. I know it’s iCloud related from my conversations with Apple Support and because I always receive a notification that says I have to sign my Apple Watch into iCloud via my iPhone.

Note that there is no option to do so in the Apple Watch settings on the iPhone. An Apple Watch is signed in to iCloud when it is paired to an iPhone.

Dwight’s fix has worked most of the time. Often it will work right away. Other times I won’t be able to sign back in immediately, resulting in an endless spinner that eventaully times out.

One of the other odd things about this workaround is that often executing it on one of my Macs will fix the situation on both. Sometimes it will require me to execute the fix on each Mac. Occasionally it will fix things on one Mac and not on the other even when executed on both. There seems to be no rhyme nor reason to this riddle.

I’ll know the workaround works when I get a notification that tells me WiFi calling is now an available option on my Macs follwed by notifications on my iOS devices that a new Mac is now available in iCloud. Which is strange given that a check of Settings always reveals both Macs being available on the account before, during and after the event.

When this doesn’t work I’ll perform a dance of the devices, turning them off and on in various sequences. Sometimes that works. Sometimes not. Sometimes I just need to wait things out and eventually things will right themselves.

That waiting corresponds with what I and other users have been cryptically (often very cryptically) told by Apple Support. Here’s a quote from Dan Moren’s experience:

. . . 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.”

I and others have also been told to wait 24 hours. Regardless of the length of the waiting period the “I can’t tell you any more than this” is always consistent.

Some Theories

I can’t offer any conclusion about the events of April 27 beyond what I’ve previously stated as speculation. What I can offer is that whatever caused that issue and how it was rectified by Apple has many similarities with these ongoing iCloud issues.

What is consistent is that they resurface each time Apple issues a beta update for iOS and macOS or a full release of same. What’s inconsistent is that sometimes the issues surface the morning of a release, sometimes the day after, sometimes the day before. NOTE: I do not run Betas on any of my devices.

What this tells me is that concurrent with those device operating system updates, beta or otherwise, Apple is issuing corresponding updates on the iCloud backend. That’s only logical, and it points up a flaw in the process. If you’re a beta tester you can and should expect issues. That’s what betas are for: to find issues. However, If you’re NOT a beta tester you should not be subjected to issues related to betas.

When I’ve raised this timing issue with Apple Support I’ve gotten tacit agreement that it is an issue, but no definitive answer. My support dialogues through much of 2024 have consisted of me sending sysdiag files to Apple each and every time an OS update is released.

However, while I still religiously collect sysdiags to send each time the issues occur, the requests to send them stopped in March. That followed a period of time when I was asked to wait until after the next point release before submitting any further updates.

There was also a moment last fall when I was told that Apple engineers had recently put the issue back under investigation after the officlal release of Sonoma. I was told they thought they had solved it with Sonoma but realized shortly after they had not.

My theory of the moment, which I’ve expressed to Apple Support and gotten no official response to, is that with WWDC quickly approaching Apple has once again has put this on the back burner for current users in order to possibly address it in the next OS release. If my theory holds we might see the issue disappear at some point in this summer’s beta cycle or it will continue as it has since the days of Monterey.

Another theory I have, and that may tie in with the events of April 27, is that this somehow relates to when a user first set up an Apple ID. My initial Apple ID was a mac.com address and that’s followed me through the MobileMe era into the iCloud era. A number of users who experienced the problems on April 27 had mac.com addresses. I can’t speak to whether or not that was always the case with every user, but in trying to find solutions to my ongoing problems, many I’ve spoken with also acquired their first Apple IDs in the mac.com era.

Note that my wife and the family members I support all began their relationship with Apple in the iCloud generation. None of them experienced issues on April 27. None of them have experienced any of these issues that continue to plague me. That’s a small sample, but it fits within this theory of mine. I’ve also heard from some others who did not experience this April 27 issue that some have mac.com addresses at the root and some do not. So again, who knows?

Bottom Line: Fix and Communicate

Apple needs to solve whatever this long running problem with iCloud and Apple needs to communicate with its users and support personnel better. Certainly they need to do so when there are more acute failures such as that which occured on April 27, whether they be security related or just attempts to find a better solution. A week is much too long to wait for some sort of statement. We may all be At The Mercy of The Backend, but we don’t need to be at the mercy of poor communication. That’s a choice by a company. Contrary to what some might think or fear, saying there’s an issue and we can’t yet pin it down is a less bad PR move than going silent.

I use Apple products and follow Apple news throughout the evolutions of beta cycles into full blown releases. I like to follow that news. I don’t like and choose not to live and work through them. Each time Apple tries to improve things or add new features I know I’m going to experience failures before I can actually use the products and ecosystem as designed and advertised. And even after the situation may be fixed, worked around or righted, so far there’s no solution that has been able to solve the problems. To me that’s unacceptable.

It reminds me of days from my youth when I’d go out to start my old beater of a car and hold my breath wondering if it would actually turn over and start. Always a relief when it did. Always a pain in the ass when it didn’t and I’d have to lug out the jumper cables. Apple doesn’t make or sell beaters. But these issues sure are beating me down.

You can find more of my writings on a variety of topics on Medium at this link, including in the publications Ellemeno and Rome.