WWDC 2026: Between Seasons

It’s my last day at Apple Park for my seventh in-person WWDC, and as I’m waiting for my final briefing just outside the Steve Jobs Theater – ever so magnificent in its polish, and yet always so strangely calm a place – I keep returning to a thought that’s been circling my head, begging for attention. I’ve never felt so “in between” phases of my career. Physically in this very moment, of course, as I’m literally sitting on an also-polished wooden bench overlooking one side of the ring, watching groups of people climb the hill to the theater and others leave. But more so mentally, insofar as I don’t recall another WWDC that’s made me feel so aware of how much things are changing around me.

At my first WWDC in San Francisco in 2016, I didn’t feel like I belonged. I was a 28-year-old blogger from Italy and somehow found my way to the most important event about the software I loved writing about. It was uncomfortable: what was I even doing there, taking notes on an iPad while folks from The New York Times or Wall Street Journal prepared articles that millions of people would read? But I didn’t mind it. I was in the middle of change; the discomfort fueled me.

10 years later, as an almost 38-year-old blogger from Italy who’s wondering just how, exactly, Apple managed to hide speakers playing music in the bushes outside the Steve Jobs Theater, I look at the content creators who are possibly experiencing their first WWDC, and realize: how am I still here, and still taking notes on an iPad, while these younger folks are shooting videos that millions of people will watch? I’m in between changes again, but I don’t mind it. The challenge still feeds me. I’m more comfortable now, but – miraculously – I don’t feel cynical or jaded. Some people are into that sort of attitude; I’ve always preferred to put in the work to be critical and enthusiastic about the things I like. In a world of complaints, optimism is a skill.

The music is still mysteriously coming from somewhere around the bushes. My friend Myke walks out the theater and tells me I’m going to love the session downstairs about AI on the Mac. “Who would have thought I’d be into that someday”, I think to myself.

The first time I noticed this newfound feeling of being “in between” eras of my relationship with Apple earlier this week involved two chairs.

It’s about 15 minutes after the keynote, and John and I are walking to a structure adjacent to Apple Park – the Developer Center where Craig Federighi will share more details about the just-announced Siri AI and its technical architecture. My brain is still processing everything, and the questions are pouring in. How does iOS 27 handle the split between on-device models and cloud-based ones? To what extent did Google help with the cloud models? Does the new Siri AI actually work in practice?

It’s a brisk walk, and, somehow, we end up sitting in the second row of the venue, right in the middle. More people start coming in. Joz sits down in front of us and to the left. The small theater is soon packed with members of the press and, just above the chatter, you can hear the faint sounds of cameras clicking and GoPros on gimbals beeping – more contrast between eras, I think to myself. Slowly but surely, you can see a crew of senior Apple PR people, plus Joz, flank two empty chairs, right in the middle, right in front of me.

I barely have time to realize how good a call I made with the seats before the occupants of the chairs claim their spots: John Ternus walks in first, and Tim Cook follows. That’s when it hits me.

You see, I never got a chance to meet Steve Jobs. I, and millions of other Apple observers and fans, also never got to experience the transition phase from Jobs to Cook because the tragic circumstances of Jobs’ passing stole that from us, and from Apple itself. We, and Apple, never got to witness what a mature, wiser, perhaps less email-prone Steve Jobs could be for the company. Fuck cancer, always and forever.

But this time, the changing of the guard is sitting in front of me. They’re intently listening to a technical deep dive about LLMs, system orchestrators, and Private Cloud Compute. They’re quiet, still, and focused.

Perhaps it’s not the most poetic image, me having a deep realization about my career and the company I write about as I’m staring at the back of two men’s heads. Whenever you’re lucky enough to find it, you have to receive life’s poetry – even when, and especially if, it makes for a funny story to tell. That moment encapsulated the energy I would feel for the rest of the conference:

We’re witnessing the sunset of an Apple era, and most people I talked to were buzzing with excitement for the next one that will soon be upon us.

What role will Tim Cook grow into? What will John Ternus’ Apple be like? What kind of leader will he be?

The event is soon over. John and I shake hands, and the thought keeps begging for my attention.

The second time the thought came back, I was watching someone demo the new Siri AI across multiple Apple devices. Going into this event, I was very skeptical that Apple could deliver on their failed promise from two years ago in a way that wouldn’t feel anachronistic compared to what other AI companies are doing now. But as I’m watching the demo, I realize: it’s the old Siri we know and (very rarely) love, but it’s doing something entirely new and different from other AIs.

The new Siri AI is, of course, reminiscent of a chatbot at a surface level. And yet unlike Claude, ChatGPT, or Gemini, the chatbot is not the product here: the chatbot is merely one of the shapes the new Siri AI can take. “It’s a feature, not a product”, Jobs would quip. The new Siri uses a collection of LLMs to deliver a personal assistant experience that, unlike others, can tap into the rich tapestry of device context and app data that other chatbots can’t aspire to. It can work with voice, it can work with text; it can be a glassy bubble in the Dynamic Island, and it can be an app. I saw Siri pull up messages from months prior and compare responses in tables generated on the spot. I saw Siri cross-reference an Apple note against an email and provide a useful response in about five seconds. It was Siri, but it also didn’t feel like Siri.

If Apple can stick the landing this time – and for all intents and purposes, it sure seems like they will – what does it mean to have a truly personal and private assistant that can retrieve data from, and perform actions in, any app on our devices, just by using natural language?

That is the moment when I get distracted by the thought during my briefing. (I hope they didn’t notice.) Sure, there’s an LLM behind it and “world knowledge” and everything, but the new Siri AI will only be as useful as the apps you use that integrate with it. And it just so happens that I’m right here at the event where the creators of the built-in and third-party apps that will work with Siri have gathered. The people behind those apps.

I’ve been thinking about this theme a lot. As Anthropic and OpenAI release increasingly powerful and impressive models, they do so by centralizing capabilities, and thus user lock-in, inside them. And I know, because I’m part of that trend: when I use Codex with a CLI and just “talk” to a model and get things done via text, I barely see the apps behind all that anymore. It’s just text: inputs and outcomes. And part of me now wonders if that happened because, over the past two years, we had no alternative on Apple platforms, so we ended up delegating assistant functionalities to chatbots and repurposing coding agents that weren’t designed to be personal assistants after all.

I’m sure that the new Siri AI won’t be nearly as powerful as Codex or Claude Fable. But maybe it doesn’t have to be. A truly personal and private digital assistant is supposed to be smart, fast, and capable of doing things my way, with the devices I have and the apps I like to use, made by people who continue to surprise and delight us every year.

There’s something else, too: no other company puts together an event like WWDC, which connects people who, in the face of vibe-coded slop and agentic dopamine, still give a damn about software made by and for humans, like Apple still does. Certainly none of the major AI labs do. Despite everything, the people are still WWDC’s beating heart.

Mind you, I was distracted by this thought for 30 seconds during the briefing, not several minutes. But it stuck with me again.

I make a mental note, tell the thought to keep waiting, and return to the demo.

I’m walking up to the Steve Jobs Theater, accompanied by an Apple PR employee I’ve known for a while. “Remind me, how many WWDCs have you been to?”, she asks. “This is my seventh”, I reply, while trying to figure out how Apple managed to hide those speakers in the beautiful landscape that surrounds Apple Park. Are they hidden in trees? Are the rocks speakers?

“Wow, so you’re a veteran”, she adds – to which I reply that it’s a very nice and polite way to tell me I’m old now. She chuckles.

“How about ‘seasoned’?”

Seasons. I like that more than “eras” – there’s a natural, more humane sound to the word. I’ve lived through a bunch of Apple seasons. And hopefully many others will come.

We’re at the Steve Jobs Theater, and I have a few minutes for myself. I sit down on a wooden bench, the music still magically playing out of thin air. I look at the ring, and the thought comes back. This WWDC felt like something that was and something that will be existed, for a brief moment, at the same time.

After 10 years, I think I’m still hungry and foolish enough to cherish the not-knowing of what this company will become.

If you’re reading this, I hope you are, too.