My iPad Upgrade Dilemma

My M1 iPad Pro feels like it might live forever. It’s been my primary computer for over five years now, and I have zero complaints about it. It does everything I need it to do, it still feels fast, and its battery has even held up pretty well given how hard I am on it. In fact, after being updated to the iPadOS 27 beta, this thing runs better than ever. It’s an amazing device.

And yet, I find myself tempted to replace it – not because it isn’t working for me, and not because new iPads have features I want, but because I know this blissful existence can’t last forever. The M1 chip, Apple’s first in-house processor made for desktop-class computing, is a marvel; even the greatest technology eventually fades, though.

How much longer will Apple support the M1 with its annual OS releases? And when those updates come, will my iPad be able to run them well? Something about iPadOS 27 feels like a pinnacle for this device, which is incredible given its age, but I don’t want to stick around long enough to see what the inevitable slowdown looks like.

To complicate matters, replacing my iPad just got more expensive. Apple has joined other tech companies in raising prices due to soaring component costs, so the same M5 iPad Pro I was pricing out yesterday costs $200 more today.

There’s still a short window open where I can avoid eating that increase: Best Buy currently lists the latest iPad Pro for $100 less than its original price, adding up to a $300 discount over the new price. Oh, and there’s a ribbon on the page that says, “Deal ends tomorrow.”

So if I wait to upgrade, I’ll inevitably end up paying more. I’m entering a murky future, clutching my five-year-old computer and hoping it lasts me a bit longer.

At the same time, insurance against price increases and software requirements doesn’t feel like the best reason to buy a new iPad. Everything else I’d be getting – the OLED screen, thinner form factor, better on-device AI model, and improved keyboard – hasn’t been enough to convince me to upgrade on its own, so I don’t think I’d really feel like I was getting much out of the purchase. As much as I love new and shiny, it wouldn’t be a fun or productive upgrade, just protective.

Is that reason enough to part with my money and upgrade sooner than I’d like? The fact that I’m so conflicted is probably all the answer I need. Regardless, I’ll be up tonight thinking about it anyway.

WWDC 2026 Coverage

Last week was a ton of fun. With Federico and John in Cupertino for the live event, Jonathan and I handled a lot of the written WWDC coverage for MacStories from home. I got a chance to write about several announcements:

This time of year always serves as a reminder of how grateful I am to get to be a part of the MacStories team and to have the community of readers and members that we do. It all makes WWDC that much more of a joy.

You can check out our full coverage of the event with details on everything Apple announced. We’ve also got a post-WWDC edition of MacStories Weekly coming later today for members, and don’t miss Federico’s essay reflecting on the week as a whole.

I hope everyone enjoyed WWDC. On to summer beta season!

Watch History Journal 2.3

It’s hard to believe it’s been over two years since I released Watch History Journal, my shortcut for logging your TV and movie watch history in a journal app on Apple devices. I’m always delighted when I hear from someone who uses the shortcut and finds it valuable. I’m still using it daily as part of my own journaling practice, and today, I’m releasing a small update to Watch History Journal.

Version 2.3 includes the following changes:

  • a fix for entries that could be misdated when sharing to Everlog (Thanks to Miles Jefford for reaching out abut this one!)
  • full support for the Journal app on iPad and Mac

This shortcut is one of my longest-running public projects, and I love being able to continue working on it and improving the experience for those who use it. My plan is to keep at it as long as I can – or until Apple Sherlocks me! 😅 My thanks to everyone who’s tried it out, offered feedback, and made this project the pleasure that it is.

You can download Watch History Journal 2.3 here.