Why I'm Building Orchard

Every year, without fail, it starts with a phone call.

“Should I upgrade to the new macOS?” my mom asks. Or my aunt. Or a friend of a friend who somehow ended up in my contacts as the family’s designated Mac person. The question sounds simple. The honest answer rarely is.

I’ve been working in the Apple ecosystem for thirty years. I’ve shipped apps. I understand how upgrades work, what can break, what to watch for. But when someone calls me from across the country asking whether they should upgrade their MacBook, I’m flying blind. I don’t know what apps they depend on. I don’t know their disk space situation. I don’t know whether the one creative tool they use for work has been updated yet. I’m giving advice based on general knowledge, not their actual machine.

Apple, of course, always says upgrade. That’s not cynicism — it’s just how it works. Their job is to move people forward. Nobody at Apple is incentivized to tell your mom to wait three months.

That gap — between “Apple says upgrade” and “what’s actually right for your specific Mac” — is where Orchard lives.

The initial idea was narrow: build something that gives people an honest, personalised upgrade recommendation: Safe, Caution, or Wait. Not based on Apple’s marketing, but on your actual hardware, your actual apps, your actual usage patterns.

But the more I sat with the problem, the more I saw something bigger.

The upgrade decision gets its marketing moment in June, when Apple announces the next macOS at WWDC. That’s when enthusiasts pay attention. But most people don’t make the decision in June. The actual question — should I upgrade? — lands in the Fall, when Apple ships the release and starts nudging everyone with a notification. By that point, if Orchard has been running quietly in the background since summer, it already knows your Mac. It knows which apps you use every day, how your memory and disk have been trending, whether anything in your setup is likely to cause a problem. The upgrade question gets a real answer, not a guess.

That’s where Orchard earns its subscription. Not the upgrade check. The year-round presence.

This year adds another dimension entirely. Apple just confirmed that macOS 27 (“Golden Gate”) drops support for Intel Macs — they just got their last supported release. For a lot of people, the question isn’t “should I upgrade the OS.” It’s “do I need a new Mac altogether.” That’s a harder, more expensive decision, and it deserves better than a shrug.

There’s a second use case I care about just as much, and it comes directly from my own life.

When a family member calls with a Mac problem, I have almost nothing to go on. They describe symptoms in ways that don’t map to what I’d see on screen. I ask them to read me things and they read the wrong things. We both end up frustrated.

Orchard gives me a window into their Mac — memory pressure trends, disk space, what’s running, whether their apps are compatible with the next macOS — all shared privately through iCloud — from another Mac at launch, and from a native iOS app early next year. No screen sharing. No credentials changing hands. No “can you install this remote desktop thing.” Just the information I need to actually help.

For millions of people who informally support family members with Apple devices, this relationship exists already. It’s just painful. Orchard formalises it in a way that respects everyone’s privacy and doesn’t require anyone to give up control of their machine.

I’m building Orchard because the problem is real, the gap is clear, and nobody else is filling it honestly.

If you’re someone who wants a straight answer about your Mac — or someone who wants to be a better helper for the people you care about — Orchard is for you.

It launches this fall alongside macOS 27. Follow along at theorchard.app, where you can “Follow the Build” and sign up to be notified about early access this Summer!

Thanks for reading.