Siri's Struggles and Apple's AI Challenges

If you want smart, nuanced insight into Apple’s products and would-be products, you turn to John Gruber, who’s been blogging about this stuff for more than two decades at his Daring Fireball site.

So in March, when Gruber announced that Something is Rotten in the State of Cupertino — focusing on Apple’s botched plans to imbue its ailing Siri service with state-of-the-art AI — lots of people paid attention. Including, apparently, folks at the very top of the Apple org chart.

I talked to Gruber about the fallout from that post. Which is pretty interesting! But there’s a lot more going on in this conversation. It’s partly about the friction Apple has been generating lately — not just about its AI efforts, but the way it runs its App Store, and the way it interacts with developers — and why all of that does and doesn’t matter.

And it’s also about the delightfully retro practice of running an ad-supported blog in 2025. That works very well for Gruber, but it seems like the new Grubers of the world are doing their work on YouTube or Substack. He’s got some thoughts about that, too.

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