Another bit of follow-up on squircle jail on MacOS. The most-asked question in my inbox from readers is this: Is mandating the squircle a concession to the much-rumored upcoming touchscreen MacBooks?

No.

The visible shape and appearance of an app icon is unrelated to its clickable — or, perhaps soon, tappable — area. Rendering a visible squircle doesn’t change the shape of the clickable/tappable target area around an icon. In the bygone days when MacOS permitted delicious app icons — and Apple crafted delicious icons for its own apps — you could click in the middle of, say, the QuickTime Player icon and it just worked. It would have been pretty nutty if it didn’t.

“Yeah, who’s this?”

“You know who this is.”

“Yes I do, yes I do. I sent a guy to deliver the package ... he didn’t call. Is everything alright?”

“Tell you what. Forget the money.”

Chance Miller, 9to5Mac: The lawsuit names Chang Liu and Tang Tan as two of the defendants. Tang Tan served as VP of product design at Apple, leading iPhone and Apple Watch product design. He departed the company in February 2024 to work with Jony Ive. Chang Liu, meanwhil...

Berber Jin and Anissa Gardizy, reporting for The Wall Street Journal (gift link): Fidji Simo, OpenAI’s No. 2 executive, plans to step down from her full-time role after an extended medical leave. She communicated her decision in a note to staff Thursday, saying that her ...

Zac Hall, writing at 9to5Mac about OpenAI’s sprawling product announcements today: To summarize today’s desktop app changes: The existing ChatGPT app is now ChatGPT Classic. Codex is now the new ChatGPT desktop app. It still looks like Codex and includes the Codex icon...

Some historical follow-up regarding just-click-it launching and apps as tiled buttons with a uniform square shape. Back in the System 7 era in the 1990s, Apple sold (sold!) a product called At Ease (via Nathan Lineback’s venerable GUI Galley): I don’t recall ever usin...

What gave Tim Cook’s privacy letter heft in 2014 wasn’t just the clarity of its plain language, but the fact that you didn’t have to take his word for it that the ads Apple showed you respected your privacy, because Apple didn’t show you ads in 2014.

Eli Tan, reporting for The New York Times (gift link): The company’s new A.I. image generator has a surprising twist: It allows people to use images from public Instagram accounts. When Meta unveiled an artificial intelligence image generator called Muse Image on Tuesda...

App icons in MacOS are not mere buttons. You can drag them, move them, and drop things on them. You click them to select, and double-click to launch. They are richer objects that deserve a richer visual vocabulary.

Back in the primordial days of AI, Parry was an ELIZA-style chatbot created by psychiatrist Kenneth Colby to simulate the words of a paranoid schizophrenic. Someone had the genius idea to connect it to Eliza (a.k.a. “Doctor”). Vint Cerf published the transcript as an RFC in 1973, and I laughed my ass off reading it. A taste:

Do you know anything about bookies?

What makes you think I know anything about bookies?

A bookie didn’t pay me off once.

What does that suggest to you?

I beat up the bookie who did not pay off, and I thought he might use his friends in the underworld to get even with me.

What else would you like to discuss?

What do you know about racketeers?

Thanks to Bob Peterson for the link.

Vint Cerf, by the way, retired from Google last week at the spry age of 83.

Tyler Hall:

We all know about macOS Tahoe’s terrible app icons and how 3rd party developers have been confined to squircle jail.

If you’re lucky enough to distribute an app outside the Mac App Store, you can break free of squircle jail using NSDockTilePlugIn. It’s not strictly the intended use-case of that API. And it’s not allowed in the Mac App Store, either. But it can solve the problem.

So today’s release of Iris adds three additional app icons to choose from in the app’s Special Preferences Settings pane. And since they use the NSDockTilePlugIn API, the custom icon remains even when you quit the app.

Iris is far from the only app using this or other techniques to sort-of escape squircle jail. All the apps I’m aware of doing something like this are Mac-assed apps. It’s a good litmus test.

After reading my posts earlier today about Eliza, the first “hit” chatbot from the 1960s, DF reader AP sent me a link to the Kickstarter page for Searching for SmarterChild, a project from documentary filmmakers Lindsey Sitz and Zan Gillies to make a movie about SmarterChild, an AOL Instant Messenger chatbot that once had 30 million “friends” (a.k.a. users). I don’t recall ever hearing of SmarterChild before, let alone using it. (I think I was on a very different level of the Internet back then.)

But this looks like a great indie nerd documentary. The Kickstarter campaign has just one week left and they’re a wee bit short of their primary goal, and quite a bit short of their stretch goals. I just chipped in.

I vaguely recall first trying some version of Eliza back in the 1990s. I never found it all that impressive nor understood its stature in the AI literature. It’s better than a bunch of if/then statements but not by much. There’s some natural language grammar parsing that is ...

The Eliza Archaeology Project: ELIZA is the original and highly influential chatbot that launched the genre of human-computer interactions using text-based agents. It was created at MIT in the 1960s as part of Project MAC by it’s [sic] designer and programmer, Joseph Wei...

Dr. Drang, in a post replete with examples of icons of popular apps from the original Macintosh, in their one-bit glory: You can see that Apple liked the idea of app icons being a tilted rectangle with some image inside the rectangle to indicate what the app did. The han...

Users expect apps and agents to reach the tools they already work in. Every integration that gets you there is a different OAuth flow, a different token lifecycle, weeks of infrastructure before you write a line of product code.

WorkOS Pipes handles it with one API call. Pre-built connectors for GitHub, Slack, Salesforce, Google Drive, and more. Pipes handles OAuth, token refresh, and credential storage. You call the real provider API with a fresh token, every time.

Connect to 100+ providers →

Sarah Perez, writing for TechCrunch: With the latest iOS 27 developer beta, Apple is giving testers an early look at one of the upcoming improvements to its AI-powered Siri: the ability to adjust how quickly and expressively the AI assistant speaks. In iOS 27 beta 3, out...

Shape was often the most iconic thing about an icon. Now it’s no part at all.

The third developer betas of Apple’s 27 OSes dropped today, and this new page in Apple’s developer documentation drew my attention — a built-in Uniform Type Identifier for Markdown data:

The identifier for this type is net.daringfireball.markdown.

This type conforms to [utf8PlainText].

My main link here is to the Swift documentation, but it’s available in good old Objective-C too.

I had previously recommended conforming to public.plain-text but stated that the text encoding should be UTF-8. I’ve updated my own recommendation to public.utf8-plain-text to enshrine the UTF-8 encoding. (Back in 2004 UTF-8 support was far from universal. Today it is.)

There’s a been a lot of (justified) concern and consternation over the last year regarding Backblaze — an online backup service whose simple pitch is that it backs up your entire computer, including the startup drive and external drives — and online file storage services lik...

Allen Pike, back in November (and corresponding Hacker News thread): Still, I wouldn’t count out the possibility of a change in course here. While mobile is king, desktop is still where work happens. While OpenAI has acquired Sky to double down on desktop, Google has lon...

A banger of an Accidental Tech Podcast members-only special, right on time. ATP memberships are just $8/month or $88/year, and the members-only episodes alone are worth the price.

They do a great job explaining what makes for a Mac-assed Mac app, but an even better job talking about why users and developers should care about them.

Maestral developer Sam Schott, on the Maestral website: As of June 2026, Maestral is no longer actively maintained. The current version will continue to work until certificates expire. Schott, on Maestral’s GitHub project page: As of 2026-07-28, this project is arc...

Jason Snell, at Macworld: My first day on the job at Macworld, Apple was perilously close to going out of business. It was the fall of 1997, and Steve Jobs had returned to Apple and engineered the ejection of Gil Amelio as CEO, but there was no iMac yet, no visible turna...

My thanks to Day One Journal for once again sponsoring Daring Fireball. Day One first launched in 2011 and has been the stalwart of journaling apps on Mac and iOS ever since. Day One’s apps exhibit a commitment to technical and design excellence, and, more importantly, every...

Yours truly, back in 2018: I don’t share the depth of their pessimism regarding native apps, but Electron is without question a scourge. I think the Mac will prove more resilient than Windows, because the Mac is the platform that attracts people who care. But I worry. I...

Flexibits: Calendar Mirroring allows you to connect two separate calendars (like work and personal) so that events from one automatically show up on the other. The best part? No event information is sent to Flexibits servers or saved outside of your device. You can cho...

Felix Rieseberg, quite obviously, is the answer to the question why Claude is an Electron app. It’s like wondering why all the screws in a building were hammered into the walls, and then finding out that the guy who oversaw construction founded and co-owns the world’s biggest hammer manufacturer.

Mike Dano, in a long (too long, I say) report for Ookla (makers of the nifty Speedtest app): Further, few other countries in the world followed in the mmWave footsteps of the U.S., with international spectrum regulators instead putting a focus on releasing mid-band spect...

Saron Yitbarek, writing on the WebKit blog, with a nice post-WWDC surprise: In Safari Technology Preview 247, we’re introducing the Safari MCP server — a Model Context Protocol server for web developers that makes your web development and debugging workflow faster and mo...