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. 

End of the Year Lists for 2022

There’s a lot I didn’t see/listen to/consume but from what I did ingest here are some thoughts. NOTE: I don’t believe in “best of.” So these lists contain what I most enjoyed.

Films:

Marcel the Shell with Shoes On

Prey

RRR

Everything, Everywhere All at Once

Guillermo Del Toro’s Pinocchio

The Howard Stern Interview: Bruce Springsteen

Spirited

Glass Onion

Continue reading “End of the Year Lists for 2022”