WWDC2025 – Life on the Wicked Stage: Act 3

Apple Beta Season Is Upon Us and iPad Debates Are Around the Corner

Changes look promising. Wait and See is the operative condition.

Apple announced what it has in store for the next versions of all of its operating systems during it’s annual World Wide Developers Conference this week. Or rather Apple put out a pretty nice commercial for some of what it has in store. But that’s the way of these things whether pre-taped or live. The beta testers and pundits are off and running looking into every nook and cranny of the code, celebrating, criticizing, and screenshotting. That will go on deep into the summer.

Apple WWDC25 iPadOS 26 hero 250609_big.jpg.large_2x.

The biggest, most observable change is the new design language, Liquid Glass, that is intended to bring all of Apple’s operating systems into a more unified look and feel, sorta, kinda based on the Vision Pro. Who knew that headset would provide new Vistas ahead?

They also unified the current OS numbering system, ditching the previous version numbers. Now each operating system will increase by the last two digits of each year ahead, as in iOS 26, watchOS 26, etc… We’re going to get to iOS 50 sooner than we thought.

I no longer play the beta game with my devices so I haven’t seen anything first hand, beyond the reactions of others that range from it’s terrible to the best thing since sliced bread. Keep in mind that any reactions you see following the release of the first developer beta should always include the caveat that what you see now will probably evolve over the course of the summer. Wait and see is the operative condition that needs to be set.

As far as I’m concerned the big news was about the iPad and what iPadOS 26 is promised to offer. There has been lots of back and forth about trying to define the iPad ever since there have been iPads. But certainly since Apple, in the pre-M1 chip era, put out the What’s a Computer campaign in 2018. There were quite a few loud voices always wanting more than Apple delivered in terms of making the iPad more like a Mac. And in recent conversations many of those loud voices were putting down their megaphones and were moving on from those iPad as their main computer dreams.

But this year Apple seems to be promising most of the changes those users have been clamoring for. They include a multiple windowing UI, much more similar to MacOS than any of the previous multi-tasking attempts. There’s even a menu bar, the inclusion of a new Preview app and more Finder-like functionality in the Files app. Better background processing and enhancements to the audio system are sure to make podcasters happy. There are a host of other new tidbits as well. There are also casualties. Many are already mourning the loss of Slide Over.

To give you an idea of how big a deal this change is, noted Windows advocate, Paul Thurrott ended his first look piece with “I may need to get a Smart Cover. Or whatever it’s called. This changes everything.”

The cynic in me has to say that the depth and breadth of these new iPad features makes me suspicious as to why Apple didn’t take this path earlier. It seems obvious that it had been thought through. The hardware has certainly been capable. Regardless of those suspicions, Apple has set up another new iPad story to keep us chattering.

So, iPads are being dusted off again. Soon, and more importantly deeper into the summer, we’ll hear how successful these features may be in fulfilling the desires of those who want the iPad to be more like a Mac. What we won’t have to wait for is the debates around the iPad to heat up.

I’ve never been one that felt disappointed by the iPad’s less than Mac-like features. For my work it has always served me well and gotten better in doing so over its evolution. Stage Manager was never my thing, but Slide Over worked well for my usage as my primary multi-tasking metaphor. Will I miss it? I’m sure I will. But I’ll wait and see what this new multi-tasking UI offers before rendering judgment.

But that’s me and I’m not everybody. So, as I look forward to living vicariously through the summer as others poke around these new changes, let me close with this. Regardless of whatever differences exist between the iPad and the Mac they always had one great similar strength that these new changes appear poised to make stronger still. Different users with different needs can use an iPad or a Mac for just about anything they want and need to do.

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.

Sunday Morning Reading

There’s a creeping inevitability to much of what’s happening around us.

Some Sunday’s when I sit down to collect what I find interesting enough to share it seems like things around us are just bad. Or going from bad to worse. It feels inevitable. This is one of those Sundays. Nevertheless, there’s some good writing and good thinking in the articles linked below that I believe are worthy of your attention. But paying attention is not one of our strong suits. Cue up a little Crosby, Stills, Nash and Young, pay attention, and read away.

‘Tin Soldiers and Nixon’s Coming’ is an excellent look back as we stare at this moment we’re in from Robert Cohen and Michael Konciewicz on the 2020 50th anniversary of Kent State and Jackson State.

You’re Not Ready, is an excellent, yet somewhat frightening compilation of articles by various authors at Wired, comprising info on AI hacker attacks, grid attacks, or a GPS blackout. I say “somewhat” simply because many of us have had inklings about this. Or at least those who pay attention.

Josh Marshal of Talking Points Memo has an excellent piece on Artificial Intelligence and The Posture of Skepticism.

Mathew Ingram’s fascinating piece, How Marc Andreessen and I (and you) Created The Web is informative and entertaining history and context that’s worth your time about the time we’re in.

Paul M. Sutter tells us that A New Theory Says Time Has Three Dimensions. It ‘Really Messes Up’ What We Know About the Cosmos, Scientists Say. We seem to be doing a good job of that at the moment given our current understanding of time, so why not go ahead and mess things up.

Timothy Snyder wonders what happens with The Next Terrorist Attack. It’s far deeper than the headline suggests.

Michael Podhorzer writes about something I’ve been thinking and saying for a while: The Courts Will Not Save Us. It’s a long read but more than worth your time. Read this instead of watching TV lawyers.

Most of the articles I’ve already linked to this Sunday morning in one way or another deal with trust. That trust gap is widening these days. It doesn’t help when we do find out things that break trust, but the finding out at least helps us understand the gap better. Take a look at Aruna Viswanatha’s piece The Pentagon Disinformation That Fueled America’s UFO Mythology.

Tomorrow, June 9th, Apple kicks off its annual World Wide Developer Conference. There are trust issues there as well. These next few links contain some interesting thoughts heading into WWDC, beginning with Sebastiann De With’s Physicality: the new age of UI, which anticipates the coming design changes rumored for all of Apple’s operating systems. A fresh coat of paint may not hurt. I’m not sure it’ll help.

As I said, Apple faces a number of problems, some legal and regulatory. Jérôme Marin explains how A Simple Comma is going to cost Apple Billions in Europe. Commas can indeed cause all sorts of chaos. Just ask US constitutional scholars about a comma and the 2nd Amendment.

And to close things out, one of my favorite developers _DavidSmith talks about his optimism heading into WWDC in Let’s Get Started. I admire the optimism and the reality check approach _DavidSmith brings to this.

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.

Thoughts and Prayers Heading into WWDC 2025

A new coat of paint won’t fix the cracks in the wall.

In a week Apple will unveil what it has in store for us during its annual World Wide Developer’s Conference (WWDC). Beginning June 9, the microscope will be focused more intently and with a greater scrutiny given the myriad of issues Apple is facing. That scrutiny might just overwhelm any message Apple has planned for the year ahead depending on how Apple handles it.

WWDC 2025 Apple Logo

The reason I titled this post “Thoughts and Prayers Heading into WWDC 2025” isn’t that I’m offering up good vibes for Apple as they try to work out of the messes they’ve mostly created for themselves. I’m actually hoping — most likely against hope — that Apple will finally clean up some of the annoyances they’ve neglected over several generations of iOS and macOS.

I’m not going to discuss the bigger picture issues Apple is facing here. I’ve written about some already, as have many others. Instead I’m going to focus on the smaller software reliability annoyances that add up to make me think Apple just doesn’t care.

It’s become almost a running joke that Apple allows some of these flaws to continue year over year. But I don’t find it funny. You can put new wallpaper over a water damaged section of a wall, but if you don’t fix the leak then the problem isn’t the stain on the wall, it’s you not caring. Or maybe you don’t have the money to get it fixed. Apple certainly has the money. As John Siracusa says in an excellent post called Apple Turnaround:

It’s been 15 years since Apple’s leadership last demonstrated that it’s willing to emphasize software reliability at the cost of new features. Since then, bugs in major features have been allowed to fester, unfixed, for years on end.

I’ll quibble with John on one point. If you allow a reliable, yet ignored “bug” to remain through several operating systems, it essentially becomes a feature the longer it’s not addressed.

I’m a stubborn old coot in my life as a theatre director. Deeply ingrained in my way of directing is something a mentor laid on me year’s ago. “If it’s on the stage it’s yours. If it fails or distracts, it’s your failure.”

Here’s a short list of bugs and annoyances that have existed over several versions of the operating systems and several versions of Apple’s hardware that I encounter routinely. That’s based on how I work and play with Apple hardware and software. I’m sure there are many more depending on how others use their devices.

Focus

I know there are folks who swear by the Focus feature, but to me it’s one of those features that works and then randomly doesn’t. I’d call it unfocused. I keep trying to use it, but abandoning it because I already have enough random failures in my life.

Shared Reminders Notifications

I’ve written about this previously. Shared Reminders are terrific for grocery lists and other things, especially of a checklist nature. But when you complete a Reminder, the notification needs to disappear for all of the users who are sharing the Reminder. I’ve had Shared Reminders hang around for hours after I’ve checked it off of a list.

Syncing Photos

This one just gets more and more puzzling and has become the butt of so many jokes, it’s almost become a part of the Apple brand. You take a photo on your iPhone and whenever it syncs to iCloud and subsquently to other devices is a wild guess. I get that if you’re running low on battery you may want to delay syncing. But if my iPhone is plugged in telling me that it won’t sync so that it can optimize battery it is a little silly. Also telling me syncing is paused for “optimizing the system” makes me wonder just what system is being optimized. Apple’s or mine?

Bluetooth Connectivity and AirPods

I’m a big fan of AirPods. I’m also a big fan of AirPods and the way they are designed to work within Apple’s ecosystem. When they work as designed it’s magic. When not, it is frustrating. Again, random failures to disconnect, which always seem to come at just that moment when you need to quickly plop them in your ears for a phone call are never fun. Neither is it a good time when one of your devices you might have previously been connected to refuses to let go of the connection.

Deleting Media from Messages

I support a few family members who keep their Messages set to retain their Messages forever. That’s all well and good, except this can quickly fill up storage on an iPhone. Apple needs to make it possible for users to select and bulk delete media on an iPhone the same way you can in Mail. The UI looks like you can swipe down the list of circles, but you can’t. The fact that you can only view these attachments sorted by size also makes it a more difficult chore to remove unwanted media attachments.

Shortcuts

I have a love/hate relationship with Shortcuts. Love it when they work. Hate it when something changes and a Shortcut I’ve relied on suddenly stops working or stops appearing in Spotlight. This happens more frequently in beta season even though I don’t run betas.

Beta Badness

Again, I don’t run betas on any of my devices. That said, I’ve been told by Apple Support personnel that changes are always happening behind the scenes on the backend during beta season that can sometimes affect all users. That stands to reason, given how much of what you do on an Apple device is tied into Apple’s servers and iCloud. I suspect this may only become more prevalent with Apple Intelligence as Apple tries to remain competitive with other AI providers that seem to constantly be updating their software. Perhaps there needs to be a way to create a wall or silo off users running betas from those who do not.

App Store

With M-series chips we’re able to get great performance and fast loading times from apps. With one notable exception being Apple’s own App Stores. For the life of me I don’t understand why they can’t improve performance on their own point-of-sale outlets. It’s like not cleaning the glass on the front of your storefront.

Settings and Permissions

I get that there are a large number of Settings. I don’t get that there’s such a haphazard way of addressing the problem of making them discoverable. I’m sure it’s a challenge, but the only way to address a challenge is to set it as a priority. The same is true with Permissions. Certainly there’s a way to force developers (including Apple) to send us to the correct Permissions screen to choose to make a selection.

Rules in Mail

I’ve set up a number of Rules in Mail in macOS over the years. Currently they all seem to be non-functioning, or randomly functioning. I have a suspicion this may have something to do with Apple’s tinkering with Apple Intelligence based mail categories (a feature I tried but turned off). Having to manually choose to Apply Rules is not the same as having a Rule that runs automatically. It defeats the purpose. Let’s face it, no company has found a way to win the cat and mouse game of spam filtering. I doubt they ever will even with AI. The Rules feature wasn’t perfect, but when it worked it was a help in weeding out some of the spam.

Consistency between iOS and macOS

Speaking of Mail, I’d like to see consistency across the board regarding features between the macOS and iOS versions. In fact, I’d like to see consistency across the board in all of Apple’s native apps. This is especially true given that there is a rumor that Apple is redesigning most of its operating system user interfaces to try and unify the look and feel between different device categories. Carry that through with how you treat app functionality between platforms. Other examples include Shortcuts and Apple News+. I enjoy being able to open an article via the Share Menu from Apple News in Safari on a Mac. I should have the same option on iOS and iPadOS.

As I said, these are mostly annoyances. But I’m annoyed that no one at Apple seems to be annoyed enough to take care of 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.

Sunday Morning Reading

When caring becomes a commodity, should we care more or less?

Lots to care about. On all the usual fronts. But in the grand scope of the universe does much of it really matter? Some interesting links to share in this week’s Sunday Morning Reading.

Dan Sinker, taking a look at The Chicago Sun-Times AI flaps calls it The Who Cares Era. His theory is that along the way, nobody cared. I’d venture they cared about the wrong things.

Apple’s annual developer conference WWWDC is a week away and given the many issues the company is confronting lots of folks care and are curious about how Apple begins to address them. Some don’t see Apple changing how it deals with developers, like Aaron Vegh in his post, They’re Not Going to Change.

Some, like John Siracusa, are rooting for Apple and even offering advice. Siracusa’s piece Apple Turnaround is a companion to his recent previous post Apple Turnover. All worth a read, regardless of how you feel about the predicaments Apple finds itself in.

The tech bros who seem to be in the pole position running to rule the world may be making bank, but they’re not winning any friends in the process. They most likely don’t care given that they think they’re on their way to conquering the universe. John Kaag is offering up A Reality Check For Tech Oligarchs. Frankly, I don’t think they live in anything close to reality.

Meanwhile, down here on planet reality, some are looking for ways to survive and perhaps beat the odds seemingly stacked against us. A.M. Hickman lays out a vision for How To Live on $432 a Month In America.

Much of what’s going on around us might seem profane and vulgar, leading to quite a few expletives coming out of our mouths as we cope. David Todd McCarty takes us on an exploration of his love of four-letter words in Frequently Profane But Never Vulgar. For what it’s worth, all words have value in my opinion. Hiding from them is fucking stupid.

Natasha MH is Reclaiming the Joy of Struggle in an AI-Driven World. Better grab that joy while we can, because that struggle is only going to become more intense.

Just when you thought we might have begun to figure out the new landscape of insanity we’re currently struggling through, comes along Ross Anderson who informs us about The Nobel Prize Winner Who Thinks We Have The Universe All Wrong. It may someday stop expanding the way we thought and might just remain stagnant for longer than originally theorized, allowing intelligent life to continue longer than we thought. One may ask, should we care?

(Photo from Vincent Nicolas on UnSplash.)

Apple Opts Out of John Gruber’s Talk Show Live at WWDC

Is Apple simply missing an opportunity or heading into the bunker?

This is significant. Apple — under fire from many directions — is opting out of having executives participating in a now decade-long tradition on John Gruber’s The Talk Show Live podcast. Gruber made the announcement on his blog, Daring Fireball.

On the one hand, given the number of fires the folks at Cupertino are fighting at the moment, it’s easy to say you can’t fault the decision. To my way of thinking though, that’s an injured hand you’re afraid to show. If it were my decision — and granted I certainly do not know what the folks at Apple know — I’d use the other hand, with a whip in it.

Here’s why.

There’s nothing that each of the audiences Apple plays to at WWDC aren’t aware of. Who are those audiences? There are the fans, the developers, the media, and Wall Street. Like it or not each of those audiences already have enough awareness of Apple’s problems delivering Apple Intelligence, tariff battles, developer relations, and court and regulatory actions. They each come in with their own set of expectations and agendas.

I would also suggest that those paying attention at WWDC — and who have read Patrick McGee’s new book Apple in China — will be approaching whatever Apple announces this year and going forward in a new context. That book not only alters the Apple narratives; in my opinion, it forces a reset.

Already I’ve seen several in the community respond to the news that Apple is forgoing an opportunity to put on a human face and connect in the midst of all that’s going on. Here’s Marco Arment and Parker Ortolani to link to two.

These Talk Show Live events have indeed been a welcome side show — an opportunity to catch a glimpse of a bit of the humanity behind the corporate front. By and large I think the history of the Gruber’s event has been a net positive. Think of it like seeing the filmmakers on stage after a screening. To a certain degree I also think those days are over with the current leadership.

In this moment of high stakes on so many fronts, Apple has obviously calculated that not putting its executives in the relatively warm seat — no offense to Gruber, but the past questions and follow up have usually not been too tough — is the better bet than attempting to meet things head on.

Again, I’d argue for the head-on approach. If you ignore what your audience is already thinking you essentially ignore (and further offend) them. If ever there was a crowd that might be receptive to some honesty (admittedly PR-coached,) Gruber’s forum would be the place to find it. Does Apple need to issue some mea culpas? Maybe, maybe not. But even well coached honesty in a discussion can go a long way to creating good will. If you ask me, Apple needs more than a little of that presently.

In my professional life I’ve faced some high-stakes presentations. None on this level certainly. I may have been working to save a theatre or two, but my success or failure never had a large piece of the world’s economy depending on it. Still, the minute stakeholders assemble for such an event you only have several choices. Distract. Deny. Or be honest.

WWDC is going to happen. Arms among the audiences will be crossed, waiting for answers and clues. Apple will certainly have enough well-packaged announcements to distract at WWDC. They can’t deny their way out of the problems they brought on themselves. Being honest, however, can’t cause any more damage than has already been done.

I certainly wouldn’t want to be involved in the planning or presenting of this year’s WWDC event — even if it is pre-taped and packaged within an inch of its life. Apple has made its choice for The Talk Show Live. While the big packaged show always takes precedence, this year seems very ripe for a side show that clears the air a bit. As Parker Ortolani says, not having that will speak volumes. It is already a very loud signal about how things might play out going forward.

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.

Apple’s Long Term Challenges Complicate The Short Term

It’s not easy to sell a waiting game.

Mark Gurman offers up a relatively thorough summary of the number of challenges Apple is facing going forward in his weekly Power On column. Things always go forward. The question is always how.

The original link above is paywalled, but here’s a web archive link to the story.

And here’s the summary:

CleanShot 2025-05-05 at 09.41.06@2x.

Gurman calls this point in Apple’s history a “critical juncture.” I would agree. The many moving parts, both surrounding Apple, and of its own making, have put Cook and company squarely in that critical juncture. This comes as Apple and those that make their living talking about Apple are gearing up for this year’s World Wide Developer’s Conference (WWDC) next month.

Gurman delivers the punchline well below the headline that neatly summarizes why WWDC is not going to be able to address all of these challenges, but also why the turmoil is going to continue.

Speaking specifically about Apple’s race to catch up in the AI realm he says:

it’s going to be a while before we can tell if Apple is heading in the right direction

Perhaps that should have been the lede. He could have easily said the same about each of these challenges he enumerates.

But there’s also a larger, more encompassing challenge that makes surmounting each even more difficult. The tech world is moving at a pace that Apple is unaccustomed to. Apple’s historic long view has served it well over the years, but the window on that long view is increasingly narrowing its aperture.

Apple may spend its June introducing and setting the table for what’s coming later this year, but already most of the smart players who follow and promote Apple are shifting their focus to the bigger, and more critical, table stakes coming long after this year’s summer and fall hype cycles end. The now familiar “coming later this year” now means much less when the real issues may only begin to be addressed further down the road.

Waiting “a while” is not an easy sell. Especially these days.

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.