Boris Cherny, head of Claude Code at Anthropic, was interviewed by Diana Hu on stage at Y Combinator’s Startup School 2026 last week. Starting around 20:30 in the video, he briefly discussed directing Claude to perform difficult tasks:

Cherny: I think the skill nowadays is less about prompt engineering and more about figuring out how do you give Claude a hard task that seems a little bit too hard. Then how do you make it possible for Claude to verify its work along the way? The verification is probably the single most important thing that people do not get right, largely.

One example of this is people were — we have this desktop app for Claude and it’s built using Electron. We’ve made it quite fast. Now it’s a pretty awesome experience. Six months ago it was sluggish and it wasn’t very reliable. Now it’s pretty awesome. It’s the thing that most of the team uses. As an experiment, I wanted to see what it would feel like if it was native. So what I did is I started a Claude Tag session. Claude Tag is a new product we have. It’s just Claude running in Slack. My first question was, “Hey Tag, do you have access to a Mac OS runner on GitHub?” It said no. Then I hooked up a runner. So it was able to start a Mac virtual machine using GitHub. My second question was, I created this empty code base that was a Claude desktop app rewritten in Swift.

I asked, “Can you access this code base?” It said no. Then I gave it access and it was like, “Okay, great. Now I have access.” Then I said, “Okay, now what I want you to do is I want you to rewrite the Electron app in Swift. I want you to run the Electron app in the Mac virtual machine, screenshot it, and then look pixel by pixel. Compare it to the Swift version. Don’t stop until you’re done.”

Hu: And that was your prompt basically?

Cherny: That was my prompt.

Hu: And how long did this take to run?

Cherny: It’s still running.

Hu: When did you start it?

Cherny: It’s been a little over two weeks. So it’s like 14 days, 15 days.

I suppose this is interesting, but I don’t think it’s interesting in the way some people sending me links to this interview think it is. I don’t think this is a serious effort to create a truly native Mac client for Claude. And if it is, Cherny is going about it all wrong.

It’s not like the problem with the current Claude Mac client is merely the technical detail that it’s written with a bloated non-native framework. The actual problem is that it’s a poorly designed app written with a bloated non-native framework. The design itself is non-native. And aside from ignoring most Mac UI idioms, it’s just a bad design in the abstract. It’s bad on the web, bad on Windows, and thus of course it’s also bad on the Mac. So pointing Claude Code at the current Electron app and directing it to recreate it in Swift — pixel-by-pixel — could at best solve only the technical problems with the current app, not the design problems. I’d be more likely to use Claude if it were well designed but still written using Electron, than if it were ported to AppKit and/or SwiftUI but with exactly the current design. The current Claude app is like a shitty recipe made with shitty ingredients; what Cherny asked Claude Code to do is to follow the shitty recipe using better ingredients. It’s still going to taste like shit.

And it’s probably no wonder the task failed. AppKit and SwiftUI are made to create Mac-style apps. Trying to use them to recreate the utterly un-Mac-like Claude UI is like trying to brush your hair the wrong way. It’s not the way things are meant to go.

I also can’t let pass Cherny’s aside, re: the current Claude Mac app, that “Six months ago it was sluggish and it wasn’t very reliable. Now it’s pretty awesome.” I just launched the Claude app on my Mac, and it took 30 seconds before it was ready to use. The last 15 seconds of which, it showed the spinning beach ball cursor. When it finally finished it showed me a dickover. Maybe it was worse six months ago but this is not “pretty awesome”.

Ulysses S. Grant, in 1875:

Where the citizen is sovereign and the official the servant, where no power is exercised except by the will of the people, it is important that the sovereign — the people — should possess intelligence.

The free school is the promoter of that intelligence which is to preserve us as a free nation. If we are to have another contest in the near future of our national existence, I predict that the dividing line will not be Mason and Dixon’s, but between patriotism and intelligence on the one side, and superstition, ambition, and ignorance on the other.

Not sure if the 2020s count as “the near future”, but holy hell is that a spot-on synopsis of our current moment.

REST serves the developers building against your API. MCP serves the agents now trying to use it. Most teams treat these as competing standards and have to pick one.

They’re not rivals, they’re layers: most MCP servers just call REST internally to do the real work. The best ones don’t convert every endpoint into a tool, they design around what the agent’s trying to accomplish.

Shipping that server also means shipping OAuth 2.1 with scoped tokens. WorkOS AuthKit already speaks that spec, so you skip building an auth provider on top.

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