Intentional AI 2: The Useful Architecture

Intentional AI

On this episode of Intentional AI, Chris Bailey and I get into the part most people skip. Everybody knows you can chat with AI.

Far fewer people know how to turn that chat into a system that actually does the work. So we lay out the four pieces that make a robot useful: the harness you sit in, the context you feed it, the memory it keeps in plain files you own, and the reach that lets it touch your calendar, your email, and the web.

Chris brings a Show and Tell on the AI health coach he built, the one that reads his Apple Watch data and photos of every meal and steers him toward goals that usually fight each other.

Then we dig into Apple’s new Siri AI from WWDC, what it gets right, and why the privacy story might be the most interesting part. If episode one was the why, this one is the how.

The Virtual OS Museum Is a Time Machine for Mac Nerds

If you ever owned a Mac that booted on a chime, the Virtual OS Museum is the rabbit hole for you. Andrew Warkentin has assembled a single emulation project covering more than 1,700 pre-installed operating systems and apps across 250 platforms. Classic Mac OS. A/UX. NeXTSTEP. System 1.0 through Mac OS 9.

It ships two ways. A 121GB full bundle that runs offline, and a lighter 14GB starter that pulls each VM image down on first launch. Either one drops you into a desktop you probably haven’t seen in twenty years.

The fun of a project like this is that it is not trying to be polished. It is a labor of love by one person who wanted every operating system in one place and decided to make it happen. The full list runs 1948 to today, and stepping through it is like flipping through a textbook of computing history.

If you want to see where Apple’s modern OS came from, fire up NeXTSTEP. Most of the ideas that landed in Mac OS X a decade later are sitting right there.

One caveat. The whole museum runs as an x86 Linux VM, so don’t expect speed records on an Apple silicon Mac. You can browse the screenshots and the full list of installations at the project’s site before you commit the disk space.

Focused 258: Defaults

Focused podcast artwork

On this episode of Focused, Mike and I dig into defaults, chronotype, and capacity. Three things that quietly shape how you work whether you pay attention to them or not.

I talk about my practice of writing down my own belief systems, and what happens when you go back and read that stuff in a moment of stress. We get practical about chronotype, when each of us does our best work, and why protecting those hours matters more than most people realize. And then capacity, which is really the payoff of the whole conversation.

I also get to announce the new podcast I’ve been building with Chris Bailey. Intentional AI is out now on the Relay Network, and I’m really happy with how it turned out.

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Paste Meets MCP

Paste, the Mac clipboard manager, just added MCP support. Your clipboard history can now talk to Claude, Codex, Cursor, or any other AI tool that speaks the protocol, through a local MCP server running on your Mac.

Think about what passes through your clipboard in a week. Links, screenshots, snippets from PDFs, that paragraph you copied out of an email and promptly forgot about. A clipboard manager already remembers all of it.

Connecting that memory to a robot assistant makes it useful in a new way. Ask for everything you copied about a project this week, and the robot pulls it together into a draft or a summary without you digging through the history yourself.

This is the part of the MCP story that keeps me interested. Ordinary utilities quietly become context sources, and the robot gets smarter without you typing a single extra word into a chat box.

A word about the privacy side, because clipboards are sensitive territory. Mine has held passwords, account numbers, and plenty of things I’d never paste into a chat window on purpose. Paste puts this behind a switch. You choose which tools get access, and you can revoke it at any time. I’m glad it’s a switch and not a default, and I’d think carefully before flipping it on a machine where your clipboard sees confidential work.

Setup is simple. Open Paste’s MCP settings, turn on Enable MCP, pick your AI tool, and follow the guide.

I keep telling anyone who will listen that a robot assistant is only as good as the context you feed it. An MCP-enabled clipboard can really help.

Ethan Mollick’s Next Book

Ethan Mollick is writing a follow-up to Co-Intelligence. The new book is called Co-Existence, and he announced it this week on his One Useful Thing newsletter. It arrives October 20, and you can pre-order it now.

I really enjoyed Co-Intelligence. That book was written for the chatbot era, when working with AI meant going back and forth with a prompt box and the human stayed firmly in charge.

That world is already fading. With agents now doing real work (and sometimes doing it better than we do), the question has shifted from “how do I prompt this thing?” to “how do I work alongside it?”

That’s the premise of the new book. Mollick describes it as a book about working with AI that is sometimes, but not always, better than you. That framing rings true for me. I watch these tools nail a hard problem in the morning and face-plant on an easy one in the afternoon.

He also admits his last book had 128 em-dashes, and he cut way back this time to prove a human wrote it. I know that feeling.

I’ve already pre-ordered. Mollick is full of good ideas on this subject, and I expect this book to give me plenty to chew on when it releases in October.

Mac Power Users 853: WWDC Reactions

Stephen Robles spent the week of WWDC 2026 at Apple Park, and I spent it running betas on a slightly scratched iPhone Air I grabbed off eBay. He sat two rows behind Tim Cook during Craig Federighi’s post-keynote tech talk. I sat at my desk in a chair.

Despite this, I think we came away with the same conclusion: this is the year Apple actually delivered on the AI promises it made two years ago. Siri no longer fails at simple tasks. It found my notes about solar panels, remembered where I’m vacationing this weekend, and located a shirt receipt without me naming the vendor.

Stephen brings the inside story on what Apple said in the smaller briefings, including how the Gemini partnership actually works and what Apple meant when they said Siri AI is grounded in personal context. There’s also a solid stretch on Safari’s new custom extension builder, the Shortcuts overhaul, Photos AI, and the new Spotlight + Siri combination on Mac. More Power Users goes long on the UniFi Travel Router, which Stephen used all week from his hotel room and which I am about to test on my own vacation.

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The New Siri Doesn’t Suck

I got beta access to the new Siri AI and the first thing I asked was, “Can you check the weather for where I’ll be this weekend?”.

I’m going on vacation. I never told Siri that. It read my calendar, figured out I’d be in Hawaii, and gave me the forecast. Old Siri would have read me the weather at home, or handed me a list of web results and wished me luck.

That one answer tells you most of what changed.

For years, the truth is that Siri made a fine kitchen timer and not much else. That’s no longer true. I spent my first hour with the new Siri running it through real tasks, and it handled a lot of them.

I asked it to add a calendar event. It asked me which calendar I wanted it on. That’s a small thing, but it’s the kind of small thing old Siri never bothered with.

I keep an Apple Note about putting solar on my house. I asked Siri to find it, and it did. Then I asked whether California’s solar laws have changed since I wrote that note. It went and researched the answer, then told me how they’d changed. It found my note and then updated it from the web, all without me touching the keyboard. That’s new.

The one that got me was the email task. I told it I’d ordered some shirts a while back and asked it to find the email. I specifically didn’t tell it the vendor name. Siri found it, REI. Then I asked it to take that receipt and build an Apple Note with all the transaction details. Done. Two apps, one spoken request, no typing.

It wasn’t all wins. I asked it to set a reminder to research solar again next weekend, then asked it to drop a link to the Apple Note into that reminder. The reminder showed up. The link didn’t. A few of my requests just stalled out. It got stuck.

World knowledge held up better than I expected too. It knew the Dodgers lost, when they play next, and who’s pitching tomorrow. The old Siri would have shrugged and offered me a search.

This is a real improvement, and I want to be clear about that. Siri with context is a smarter Siri, and you can see the shape of it in these early tests. The weather answer worked because Siri could see my calendar. The note answer worked because Siri could see my notes. Context is the whole game.

Which is exactly what I can’t stop thinking about. How much context will Apple actually allow?

Letting Siri read your calendar and your notes is one thing. Those are Apple’s own apps, on Apple’s own terms. The harder question is what happens with everybody else’s apps. The tasks that impressed me most were the ones that crossed from one app to another. If that only ever works inside Apple’s walls, it’s useful. If outside developers get real, deep access to the same context, it’s a different product entirely.

Developer buy-in has never been a given with Apple. They’ll need to hand developers a reason to show up, and developers will need to trust that the floor won’t move under them in two years. I don’t have an answer there yet. We’re just days past the keynote. Nobody has had time to push on the edges.

Part of me also feels like this is Apple arriving where they should have been a couple of years ago. Context-aware assistance isn’t new. I run a whole Field Guide on building an AI assistant with deep personal context, and what I can do there runs circles around what Siri pulled off for me today. I didn’t expect Apple to match a full Cowork-level harness on day one, and they didn’t. But the gap is real, and it’s worth saying out loud.

So what I’m watching now is whether Apple keeps its foot on the gas. What shipped today is a good start. My worry is that “good start” quietly turns into “good enough,” and the effort slows down right when it should be accelerating. Context-aware assistance isn’t a feature you ship once and check off. It’s something you keep pushing, year after year, app by app.

I hope they push. The bones here are good, and that’s not something I’ve been able to say about Siri … well … ever. For the first time, I’m curious what it’ll be able to do next month instead of resigned to what it can’t do today.

Apple’s Hardware Is Waiting on Siri

It used to mean something specific when an Apple product went out of stock. The old machine sold out right before the new one showed up.

Now things go out of stock because Apple can’t get the chips, or because they’re holding back for a launch they haven’t announced. The HomePod mini has been out of stock almost everywhere for months. I get that there are supply constraints in play, but the HomePod mini?

Then you look at what the Home app picked up this year. Plain-language summaries of camera clips. Multi-camera stitching. 4K recording. These are exactly the kind of features that want a screen on the wall and an assistant you can talk to. They read like software written for hardware that isn’t on sale yet.

It seems Apple has a backlog of devices ready to go, all gated on one thing. A Siri good enough to drive them. A HomePod with a display, a real home hub, whatever the speaker-tablet thing turns out to be. None of it works without an assistant that can actually do something when you ask.

That makes this WWDC the software unlock. Apple shipped the brain first. My money is on the bodies following this fall. September, October, once the new Siri is actually in people’s hands, I’d expect a wave of new devices that suddenly make sense.

Apple Finally Owns Age Verification

I’ve been saying on the Lab Report for years that Apple needs to own the age of the person holding the device. This year they did something about it.

The piece that matters is the new Declared Age Range API. It lets an app know whether it’s dealing with a kid, and roughly how old, without the app collecting a birthday or any real identity. The device vouches for the age range. The app tailors itself. Nobody hands over private data to do it.

That’s the right way to solve this. For years the only thing standing between a child and an adult experience online was a checkbox asking the kid to confirm they’re over a certain age. We all know how well that worked.

Apple built the rest of it out too. Child accounts are the starting point, with a setup assistant that lets parents open things up over time. There’s a new Ask to Browse that works like Ask to Buy. And Screen Time, which has been a buggy mess for years, got a full redesign.

The timing isn’t an accident. Jonathan Haidt’s book The Anxious Generation got real legs. Parents are paying attention in a way they weren’t even two years ago, and you don’t hear this kind of announcement at a Facebook keynote.

So I’m glad Apple did it. My worry is the follow-through. An age-range API only matters if developers actually adopt it, and parental controls only matter if Apple keeps engineers on them instead of shipping the redesign and walking away for six years. That’s the pattern I’m watching for.

For once, though, the foundation is the right one. Now they have to build on it.

HomeKit Secure Video Hits 4K. You’re Welcome.

A couple of weeks ago I wrote a whole post complaining that HomeKit Secure Video was still stuck at 1080p in 2026. I never published it. I figured I’d look silly if Apple fixed it the week after I hit send.

Then the keynote happened. The Home app is getting 4K recording on supported cameras. So I’m taking full credit. You’re welcome, everybody.

The 4K is the headline, but there are more Home improvements. Apple Intelligence now writes plain-language summaries of your camera clips, so instead of scrubbing footage you get told what happened. Related clips from different cameras stitch together into one event. And you can search your recordings by what’s in them before you even finish typing.

That last one matters. The reason I’ve stuck with HomeKit Secure Video through the lean years is the privacy model. Footage gets analyzed on a hub in your house, encrypted before it ever touches iCloud, and the metadata describing what’s in your clips never leaves your devices in the clear. Search and summaries that run inside that model, instead of on some company’s server, are the version of these features I want.

Still, 4K is a welcome improvement and answers my biggest complaint.

I’ve recommended the Aqara line to people who want to stay inside Apple Home and still get decent hardware. For now, I’ll take the win. My footage is about to look a lot better, and I didn’t even have to publish the angry post to get it.