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Ben Thompson, in a subscriber-only Stratechery update Tuesday:

I got a fun email from former Apple executive, Nest founder, and one-time Stratechery Interview subject Tony Fadell in response to yesterday’s Update about Apple suing OpenAI (published with permission):

Good article as always… This is Apple’s typical tactic to scare Apple employees — either former or current. I heard this lawsuit was driven by the Apple board.

Steve threatened to file a lawsuit against Nest for poaching 80-100 Apple employees. He called me, screamed for a while with lots of accusations. Then I said, “Steve, it’s Apple’s job to retain its talent, not mine.” He stopped his rant and then we went on to talk about our families and vacation plans. We kept hiring…

This sounds about right — and in terms of the Steve Jobs angle, John Gruber made a compelling case on Dithering that this lawsuit may very well have been driven by John Ternus channeling his inner Jobs.

Fadell, of course, is correct that it’s Apple’s job to retain its talent. Recent reporting from Mark Gurman suggests that John Ternus is keenly aware of this, at least as it pertains to Apple’s industrial design team, which has been ground zero for the Apple-to-OpenAI recruitment pipeline. (And the Dithering episode Thompson references is the one we made free-to-listen this week.)

Playing hardball when it comes to poaching is deeply embedded in Apple’s DNA. Steve Jobs hated Apple employees getting poached. In 2005 he sent this email to Adobe CEO Bruce Chizen:

From: Steve Jobs
To: Bruce Chizen
Date: Thursday, May 26, 2005 9:36 AM
Subject: Recruiting

Bruce,

Adobe is recruiting from Apple. They have hired one person already and are calling lots more. I have a standing policy with our recruiters that we don’t recruit from Adobe. It seems you have a different policy. One of us must change our policy. Please let me know who.

Steve

After one back-and-forth exchange with Jobs, Chizen agreed Adobe would change its policy.

A more contentious example came in August 2007, when Jobs sent an email to Palm CEO Ed Colligan that read:

From: Steve Jobs
To: Ed Colligan
Date: Sunday, August 26, 2007 11:42 am
Subject: Fwd: Your proposal

Ed,

This is not satisfactory to Apple. It is not just a matter of our employees deciding they want to join Palm. They are being actively recruited using knowledge supplied by Jon Rubenstein [sic] and Fred Anderson, with Jon personally participating in the recruiting process. We must do whatever we can to stop this. I’m sure you realize the asymmetry in the financial resources of our respective companies when you say: “We will both just end up paying a lot of lawyers a lot of money.”

Just for the record, when Siemens sold their handset business to BenQ they didn’t sell them their essential patents but rather just gave them a license. The patents they did sell to BenQ are not that great. We looked at them ourselves when they were for sale. I guess you guys felt differently and bought them. We are not concerned about them at all. My advice is to take a look at our patent portfolio before you make a final decision here.

Steve

That’s a good email. Information dense. My favorite part isn’t the “I’m sure you realize the asymmetry in the financial resources of our respective companies”, although that’s good. It’s the “I guess you guys felt differently and bought them.” Stone cold.

Some backstory on the players:

Colligan, of course, is Mr. “PC guys are not going to just figure this out. They’re not going to just walk in.” He was a business guy who thought product guys didn’t matter in an industry that was about to be taken over by product guys. Sort of like Steve Ballmer, without the charisma, at a much smaller company.

Jon Rubinstein¹ was a hardware engineering executive at Apple, overseeing Mac hardware during the comeback years after Steve Jobs returned, then switching to oversee the newly-created iPod division in 2004. (Mac hardware then went under the supervision of a then-little-known operations executive referred to in the announcement as “Timothy Cook”.) Rubinstein left Apple in early 2006, citing exhaustion.² His departure was announced six months earlier, alongside the promotion of Cook to COO. By 2007 Rubinstein was involved with Palm, by way of Elevation Partners, an investment firm that took a 25 percent stake in Palm. He became CEO of Palm in 2009, tried to turn it around, and then wasted a few years as an executive at HP after HP bought Palm’s carcass thinking it was still alive.

Fred Anderson was Apple’s CFO from March 1996 (almost a year before the NeXT reunification) to June 2004 — the nail-biting, at-times-near-bankruptcy turnaround years. Anderson took the fall, perhaps unfairly, for the stock options backdating scandal under Steve Jobs and, after leaving Apple, paid a $3.5 million fine in a settlement with the SEC. Needless to say, in the summer of 2007, there was bad blood between Anderson and Apple. Anderson, post-Apple, was a co-founder of Elevation Partners and had recruited Rubinstein to join.

Some bad blood. Some former high-level Apple executives putting a team of ex-Apple engineers and designers together to take on the iPhone. History doesn’t repeat, but it often rhymes.

If in addition to thinking that this sounds familiar, you also think these emails sound illegal, you may recall that in 2015, Apple (along with Google, Adobe, Intel, and other companies) paid a collective $415 million penalty to settle a class-action anti-poaching lawsuit. That they settled doesn’t mean they regret playing hardball. Rules are only followed by those who fear the penalties.

Jobs liked to fight, and wasn’t afraid to let his temper show. Tim Cook has a fierce temper and steel nerves, but he arguably only once, ever, showed it in public. I do not think he relishes a fight. He’s a diplomat, not a general. I suspect there’s no undiscovered tranche of Jobs-style stone-cold threatening emails from Cook to competing CEOs.

Steve Jobs’s oft-cited parting advice to Tim Cook was “Don’t ask what I would do. Just do the right thing.” Cook has largely lived by that mantra. But maybe — maybe — by taking that advice to heart, he has at times deliberately steered the company in ways Jobs would not have, just for the sake of steering it in a different way. I think maybe John Ternus is more of a “Hey, what would Steve have done here?” kind of guy.

On the one hand, this lawsuit is a bad look for Apple. It could be perceived that Apple does not think their employees are free to leave and compete against them. On the other hand, Apple could use a booster shot of Steve Jobs’s “us against the world” attitude. It might be wrong to start a war, but it’s never wrong to finish one after being attacked.

What would Steve Jobs do with this OpenAI situation? He’d go to war.³

‘This Is Not Satisfactory to Apple’

The early history of the Macintosh GUI went something like this: When the Macintosh debuted in 1984 it didn’t hit like Apple had hoped it would. (That’s when Steve Jobs was run out of the company.) But by the late 1980s it had caught on, especially in markets like design and desktop publishing. It was the only GUI game in town — command-line DOS PCs were popular, but Windows 1.0 was almost too primitive to believe and Windows 2 wasn’t much better. Apple was certain that the WIMP GUI was the future of computing, and because the Macintosh was the only credible GUI then on the market, Apple owned the future of computing. They were correct about one of those things. Because then came Windows 3, which still sucked — still was ugly, still was terribly designed, still severely limited compared to the Mac in its UI grace and vocabulary of actions — but, it didn’t suck as much. It wasn’t good but it was good enough for the corporate IT market, and the corporate IT market drove the industry at the time.

In the early 1990s John Sculley filed and pushed the infamous “look and feel” lawsuit against Microsoft. One year out from the launch of Windows 95 — which at least looked pretty good⁴ — Apple’s response was to try to argue in court that they owned the copyright and patent rights to the very concepts of the GUI and the desktop metaphor. The court handed Apple its ass. Apple soon found itself 90 days away from bankruptcy and in desperate need of a new modern operating system, which they themselves had proven incapable of creating. Windows 95 launched with such anticipation that customers lined up overnight outside retail stores to buy it the morning it launched.

That lawsuit was the low point in the entirety of Apple’s history. It was incoherent and, worse, pathetic. Incoherent because Apple was simultaneously arguing in marketing that the Mac remained vastly superior to Windows (“C:\ONGRTLNS.W95”), while arguing in court that Windows was a feature-for-feature clone. It couldn’t be both. I would argue that the former was true — the Mac remained superior in many ways — but actions speak louder than words and Apple’s action was to sue Microsoft and lose. It was pathetic because you know who loses? Losers.

The correct response to the competitive threat of Windows wasn’t to futilely attempt to argue that Windows should not be allowed to exist. It was to make the Macintosh so much better than it already was — to inject so much new innovative insane greatness — that customers would line up overnight to buy Mac software (and watch Apple keynotes). What Microsoft had in 1995 that Apple could not muster was vast customer enthusiasm. That cannot be bought. It cannot be faked. It can only be earned. And you sure as shit cannot stop it with a lawsuit.

Earning that sort of consumer enthusiasm — in spades — is exactly how Steve Jobs pulled Apple out of its nosedive. It took the better part of a decade.

When Apple announced this new lawsuit last week against OpenAI, I wondered, at first, whether it had a whiff of that 1994 look-and-feel loser desperation. Is it Apple’s position that the only way to stop its talent exodus to OpenAI is in court? Upon consideration, I think not. First, it’s not incoherent. There’s no conflict between what Apple is saying about its products or itself as a company that is at odds with this lawsuit. They’re just saying, “Fuck you, you goddamn traitors. You want to fuck with us? We’ll fuck with you.” When you poke a bear — 400 times — you better be ready for the bear to eventually react.

Further, while Apple can only have one CEO at a time, and that CEO remains Tim Cook until September 1, there’s no way that John Ternus doesn’t fully approve of this lawsuit. Cook has gone out of his way to leave Ternus with a clean plate. It would be insane to file this suit six weeks ahead of Ternus taking the helm if Ternus is anything short of fully on board.

I’m not saying it’s a good look for Apple. I’m certainly passing no judgment on the merits of the case, which OpenAI hasn’t yet responded to legally. But it is a very different and much more emotional reaction than we’ve seen under Tim Cook. Those anti-poaching emails Steve Jobs sent to Adobe, Palm, and Google weren’t good looks for Apple either. But that doesn’t mean they were bad for Apple. A bad look can be a good thing. Passion is powerful, and in and of itself, inspiring. This is a passion-fueled lawsuit. I saw some commentators speculate that, already hemorrhaging cash on a daily basis, OpenAI will surely spew some of that in the direction of Cupertino and just settle it. But Apple doesn’t need cash. This is a lawsuit that I believe OpenAI cannot settle, because there is no settlement Apple would accept short of a dissolution of their entire hardware division.

Apple claims in their complaint that the trade-secret chicanery they’ve already documented “is the tip of the iceberg”. If Apple is wrong, and OpenAI has recruited above the board and hired 400 former Apple employees fair and square (or even just mostly fair and mostly square), they have nothing to fear, and John Ternus will look like a petty little jealous bitch, and a feckless one at that. If Apple is right, however, all bets are off. I said earlier that rules are only followed by those who fear the penalties. But some never consider the penalties in the first place because they believe the rules don’t apply to them. Sometimes they find out otherwise.

I’m not saying OpenAI cannot win. I’m saying they can’t get Apple to settle — at least not until Apple is satisfied the whole iceberg has been revealed through discovery. Until then, John Ternus’s offer to Sam Altman is nothing — not even the fee for the gaming license, which he would like Altman to put up.

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We met a week later at his outdoor office — a bench in SF’s South Park. He told me that he was going emeritus at True Ventures, the VC firm, and that he was going to spend more of his time writing.

It was awesome to see him. Sitting on a bench with Om could be quasi religious. He talked so softly and deliberately that it forced you to slow down, lean in and forget about everything else.

What became clear was that we actually saw the world the same way. We didn’t agree what Wired should be doing about it. But we did agree on this: While everyone was fixated on big tech, an explosion in tech innovation not seen in a generation was taking place. We both agreed that not enough people were writing about it.

“Maybe we should do something together then,” I said.

Joanna Stern:

So saddened to hear about @om. His writing was one of the reasons I went into tech journalism. Right out of college, I was working at a PR agency and started reading his site. It inspired me to start blogging.

Years later, he tried to recruit me. Even after I went elsewhere, he’d send me notes telling me how proud he was of my work. He’d often review my reviews, so here’s mine of him: Generous with his time. Honest with his feedback. Endlessly encouraging to those coming up behind him.

Casey Newton:

Very sad to hear about the passing of @om. He shared two lasting lessons with me: the first when I was a cub tech reporter at the SF Chronicle; he interviewed me for a job but told me he didn’t think I could hack it at GigaOm because newspaper writers were too slow. It taught me that I needed to get out of print media ASAP.

The second was many years later, when I was having a drink with him and some other reporters. We asked him for advice. “Never name a blog after yourself,” he said. RIP

Jim Nielsen:

One day on Twitter I got a DM from someone with the handle @om.

“I don’t know who this is,” I thought, “but damn that is a great handle!”

Then I peaked at the follower count: over 1 million!

“WTF? Who is this???” I thought.

I’d never — then or since — been contacted by someone with such a high profile online.

How was I even on this person’s radar?

Om seemingly read everything.

MG Siegler:

Looking at my emails and social media messages from back then is just a treasure trove. Om was always quick with a compliment about something I had written but also with a criticism at times. He clearly just read endlessly and couldn’t help but share his opinions, even if privately. In person too he was amazingly candid and honest. He would complain how annoyed he was if you beat him to some story — but complain even louder if he felt like he actually beat you but wasn’t getting enough credit. He was clearly competitive too. And he was correct in his assessments, because again, he was honest. [...]

To me, Om was and will always be such a singular individual. There will never be anyone quite like him. He’s the only person I know who could be both humorously downtrodden and insanely optimistic at the exact same time. Again, he just seemed to wear his emotions on his sleeve.

Jason Hiner, in a post on LinkedIn:

This is the opening anecdote from “Chapter Six: The Blogger” from my 2016 book, Follow the Geeks, co-authored with Lyndsey Gilpin. Om once told me that “For three years, it was every day a rejection” as he tried to break into tech journalism. This was how he finally broke through.

David Churbuck checked his voicemail. There was a message from someone looking for a job.

Because of the guy’s thick Indian accent, David could barely make out what he was saying, except that he worked for a wire service down on Wall Street and was a big Forbes fan. The guy heard that Forbes was going to be one of the first media companies to launch its magazine on the web and he wanted to come help.

David ignored the message. He had a small team and hardly any budget.

Then he got a fax. It was from this guy, explaining why he was a perfect fit to join the team.

The next day, the guy left another message. If David would just give him a call, it would be great to talk with him. He wouldn’t regret it.

Ignore.

The following day, he left another. Whatever time limit there was for voicemails, this guy always used up every minute.

Still, David ignored it.

And then the guy started getting creative.

[...]

One of the journalists, Michael Noer, said half jokingly, “Just call the guy in!” So, partly out of admiration, and partly out of pure morbid curiosity, David called him back.

One interview. Fifteen minutes. That was all it took for David to hire Om Malik.

“They do not sell themselves”, Om told me in a separate story from that same time in his life.

Hiner made the entire chapter available to read as a handsome PDF. It’s so good, and so utterly Om. It’s a crackerjack good read about the very early “WWW” days of the web. A bit:

Om is charming and disarming, forceful and accommodating. He has an easy smile, a quiet, melodic voice, and a handsome face. Once he opens his mouth, it’s obvious how much he reads and how thirsty he is to learn. It’s rare to meet someone who is ready to debate you on almost any topic, but who’s also genuinely curious about your life and your opinion. It all makes the burly journalist one of the most huggable people on Earth. That’s what David was up against when he met Om. He didn’t stand a chance.

“It was destiny,” said David, with a self-deprecating laugh. “It was total destiny.”

Om’s close friend, photographer Christopher Michel, published “Om the Great”, an enormous gallery of portraits of him. Here’s just one of hundreds:

Lastly, here’s a story from Andrew Sasaki, which he sent me by email, and I’m reproducing with his permission. It’s the perfect Om story:

I met Om briefly at a tech event in NYC around 2008 or so. He was talking with a friend of mine, and when I walked up he introduced himself: “Hi, I’m Om.”

“‘Om’ like ‘Om Malik’?” I asked.

This amused him greatly.

“Yes, exactly like Om Malik”, he said.

A couple of years later the iPad had just launched, and I saw my friend again at another industry event. I asked him a question related to the unprecedented development effort we were already seeing around the new platform that didn’t yet have a single compelling use case.

“You know who I bet would know about that? Om Malik”, he said, and gave me Om’s email address.

I hesitated to bother Om, but eventually reached out with my question. “I don’t know if you remember me, but we met a couple of years ago, and…” blah blah blah.

Naturally, there was no answer. Why would there be? He doesn’t know me from Adam, and he’s Om Fucking Malik.

Except there was an answer about 4 days later. Om started off by apologizing for the delay in responding, but he had taken the time to research his answer before writing to me. And of course, his answer was thoughtful, insightful, and absolutely correct. I was gobsmacked at the generosity he had shown replying to someone he didn’t even know. He gave no indication that he even remembered me until his signature line:

“Exactly Like Om Malik”

Cook’s letter is cogent and clear, and well worth reading in full today. But when you do, you can see why Apple no longer hosts a copy:

A few years ago, users of Internet services began to realize that when an online service is free, you’re not the customer. You’re the product. But at Apple, we believe a great customer experience shouldn’t come at the expense of your privacy.

Our business model is very straightforward: We sell great products. We don’t build a profile based on your email content or web browsing habits to sell to advertisers. We don’t “monetize” the information you store on your iPhone or in iCloud. And we don’t read your email or your messages to get information to market to you. Our software and services are designed to make our devices better. Plain and simple.

One very small part of our business does serve advertisers, and that’s iAd. We built an advertising network because some app developers depend on that business model, and we want to support them as well as a free iTunes Radio service. iAd sticks to the same privacy policy that applies to every other Apple product. It doesn’t get data from Health and HomeKit, Maps, Siri, iMessage, your call history, or any iCloud service like Contacts or Mail, and you can always just opt out altogether.

Some of this remains true, but has lost some truthiness — and truthiness matters. But some of it is no longer true, period. It’s no longer just “one small part” of Apple’s business that serves advertisers. Here in 2026, search results in the App Store not only show paid ads — frequently for casinos — but the search results are visually dominated by paid ads now that Apple has added a second ad to results. Apple News+ is a paid subscription that offers a genuinely great value for the number of paywalled publishers whose content it includes, but articles on the News app tend to include the weirdest AI-generated ads on the Internet. (How many young blond women am I supposed to believe need hearing aids?) And — at this writing, still “coming soon” — Apple is launching ads on Apple Maps. Apple Maps remains free of charge to use, so according to Tim Cook, we’re not the customer. We’re the product. Or, if you prefer, our frustration is the product.

I thought to revisit Cook’s 2014 “you’re not the customer, you’re the product” letter today in light of Meta’s new policy of defaulting Instagram users into having their personal content serve as grist for AI-generated content created by other users. The New York Times described Meta’s on-by-default policy as “surprising”; I say it’s not surprising at all. Meta has never shown any respect for its users’ privacy, and when they’ve claimed to, everyone knew it was a sham. They no longer show any respect for their own engineers’ privacy for chrissake.

But Apple? Apple meant it. And I think they still do. But I think they’re lost in the weeds on two fronts:

1. Squeezing out every extra cent of Services revenue they can.
2. Satisfied in their own deep knowledge of how their systems are designed to safeguard users’ privacy and personal data.

Issue #1 is self-explanatory. The ratio of ads to organic results in App Store search — especially when measured in screen area — is clearly not aligned with Cook’s 2014 statement that “Our software and services are designed to make our devices better. Plain and simple.” Obviously not. App Store search today is designed primarily to generate more revenue for Apple. That’s not criminal, but it’s a change.

Issue #2 is more subtle. Apple really does have a religious fervor for privacy. Consider ads for Maps. It hasn’t shipped yet but Apple states, “Run ads in a privacy-first environment that respects your customers, who already trust Maps. No tracking — just helpful discovery.” I’m quite sure that’s all completely true. I just wrote last week about how Apple has never had to deal with “geofence warrants” for its location services because Apple has never kept personally-identifiable usage data for location. They not only don’t give advertisers — or law enforcement — your location data, but can’t, because they don’t collect it and never did.

So let’s just concede that the upcoming ads in Apple Maps are completely private. How many users are going to believe that? Or assume it? I think very few. People see ads and they think “I’m being tracked.” When Apple starts showing ads in Maps, many — perhaps most — users are going to think they’re being tracked by Apple and their location “is being sold” to advertisers.

It’s not true. Apple knows it’s not true, because they built and control all of the systems involved. Apple is very proud that this is true, and they should be. It’s a good thing and it really is an important institutional value at the company. It’s a religious fervor. On this particular issue Apple really is set apart from its peer-sized companies in technology.

But that’s not what the general population believes. The general population thinks of “Big Tech” as a single, almost unified, hegemony. A lot of “Apple users” only use one Apple platform, the iPhone, and if they own another Apple product or two they’re iPhone peripherals like AirPods and Apple Watch. If they believe Apple is ethically better with regard to privacy (or anything else) than other companies, it’s only a little better. Most people have no idea whatsoever how anything Apple sells actually works. It’s all magic. That’s why a majority of adults believe that apps on their devices surreptitiously listen to and record real-world conversations in order to show them eerily-accurate targeted ads. Apple has actually done a lot of hard engineering and design work to guarantee that software on your devices can’t surreptitiously listen to you. But most people don’t know that and wouldn’t understand it if it were explained to them. All they know is that they were talking about Frisbees the other day, after not having uttered the word “Frisbee” in years, and now they’re seeing ads for flying discs in Instagram — and the only explanation that makes any sense to them is that their phone “listens” and betrays their privacy.

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 2014.¹ Apple today can’t say that. Apple can prove to itself, and to technically sophisticated outsiders who are willing to listen, that it can serve ads — even in Maps — in privacy-protecting ways. But the only way they can prove to most people that they’re not betraying the privacy of their location data or app usage is not to sell such ads in the first place. Seeing is believing, and when people see ads in their maps app, they believe they’re being tracked.

John Ternus should return Apple’s privacy policy to its 2014 clarity. The trust Apple would earn from such a move would far out-value whatever revenue these ads pad to their already hefty and ever-increasing quarterly Services numbers. “The companies that offer you services free-of-charge to show you ads are betraying your privacy and disrespecting your attention” is a powerful marketing message that only one major tech company used to be able to credibly make. That’s always been a resonant message, but never more so than today, in the age of AI. Ternus should make the slight course correction needed so that Apple can hammer that message once again.

But iOS app icons (and iPadOS) were always in squircle shape. Why is and was this okay for you, but it’s not for macOS?

This is a good and fair question. But I not only have an answer, I have an answer that clarifies why this entire debate is important. That “design is how it works” applies even to something as seemingly superficial as icons.

There are all sorts of limitations and simplifications in iOS that would be bad ideas to bring to MacOS, which would range in effect from disappointing to frustrating to maddening to ruinous. Where squircle jail falls on that scale is subjective. It’s certainly not ruinous, but I’d say it’s maddening. (iOS baby-computer-isms that would be ruinous to bring to MacOS would include killing AppKit, removing the Unix terminal layer, or requiring all apps to come from the App Store.)

MacOS has suffered many such frustrating decisions before. E.g., it arguably makes sense for iOS to omit always-visible scroll bars because screen real estate is so limited. It makes no such sense on the Mac.

As for mandatory squircle shapes for app icons in particular:

(a) I don’t think this is a good mandate for iOS either;

(b) it was always so for iOS, though, so it’s not like Apple has ever taken away rich creative icon shapes on the platform;

(c) MacOS is a far richer and more precise environment than iOS.

App icons on the iOS home screen are effectively simple buttons. I think it’s rather obvious that’s why they have had that squircle/roundsquare shape ever since the iPhone was announced in January 2007 (source). They’re one-tap launchers. 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. iOS is a world meant for fat-tipped Magic Markers and blunt safety scissors. MacOS is a world meant to support fine-tipped drafting pens and precision razor-sharp X-ACTO knives.

Plus, Macintosh icons have four decades of glorious history. Style and fashion change over time. But limitations should not be imposed where freedom once reigned.

And shape as a differentiating factor is not mere decoration. We have long known this. We all knew this. And not only did Apple know it, the rest of us knew it because we learned it from Apple. Via the Internet Archive, here’s Apple’s Macintosh Human Interface Guidelines from 2018,¹ which was not that long ago:

Consider giving your app icon a realistic, unique shape. In macOS, app icons can have the shape of the objects they depict. A unique outline focuses attention on the object and makes it easy to recognize the icon at a glance. If necessary, you can use a circular shape to encapsulate a set of images. Avoid using the rounded rectangle shape that people associate with iOS app icons.

“A unique outline focuses attention on the object and makes it easy to recognize the icon at a glance.” Eight short years ago. That is not the description of a fad or fashion. It is a description of human perception. Our unchanging nature.

So much collective hard-earned wisdom has been ignored of late. But it’s not lost or forgotten. Chapter 11 of the 2002 Aqua Human Interface Guidelines is a good place to start remembering. There was tremendous thought, rigor, and logic behind those guidelines — all of it in the name of creating a visual language for icons that most people simply thought looked cool as fuck.

Apple’s prohibition on shapes is a step backward for both usability and creativity in app icons. Icons are now harder to distinguish because they’re no longer allowed to be distinctive. But there’s no technical reason for it. Apple could, and should, once again allow icons to take on a wide variety of shapes.

It’s clear that some people within Apple recognize that the transition to Liquid Glass introduced mistakes. They also appear to have the authority to fix those mistakes. Refinements to Apple’s own icons in Golden Gate are a welcome course correction, as is the much-celebrated Liquid Glass opacity slider. It’s time to correct the mistake of banning icon shapes as well.

Apple should stop forcing every icon into the same squircle.

The squircles, I will point out, are not in and of themselves the problem. The problem would be the same with any mandated shape, like, e.g., VisionOS’s circles.

John Siracusa:

Squircle Jail is the worst design-related thing Apple has ever done to Mac developers, and probably the worst icon-related thing it has ever done, period. Incredibly developer-hostile.

If squircled icons are actually better, then let that design win in the market. That’s how we transitioned from the classic Mac OS icon style to the more photorealistic Mac OS X icon style. Developers adopted it because they wanted to, and because users desired it.

John Siracusa has a long memory, cares deeply about Mac design, and is not prone to hyperbole (putting it mildly). I’m not sure I agree with him that this is “the worst design-related thing Apple has ever done to Mac developers”, but it’s certainly on the short list for consideration. And, like Siracusa, I can’t think of any other design crime Apple has ever foisted on Mac developers that I’d argue (with Siracusa) was worse.

It’s one thing for Apple to force all of its own app icons into the same identical shape. That would be bad enough, because Apple’s own Mac apps are numerous and popular, and as the platform owner Apple necessarily sets the direction that many third-party apps follow. But it’s just downright spiteful to enforce it platform-wide. Apple decided they’re no longer going to create nice icons with unique, interesting, and most importantly, distinctive shapes — but they no longer allow third-party apps to either. It’s like Apple decided every single one of its own apps must wear a stupid-looking hat, and they put those stupid-looking hats on third-party apps too, whether the developers of those apps want them or not. Scratch that. Not hats but helmets. The mandatory squircle makes identifying apps at a glance harder in the same way that it’s difficult to identify individual people if they’re all wearing same-shaped helmets. Real helmets at least serve an important safety purpose. The squircles are like stupid unnecessary helmets.

To that point, Jim Nielsen draws an even better analogy — traffic signs:

Consistency for traffic signs! Let’s start by redesigning them all to be the same shape.

Which was a sarcasm-dripping reply to his own previous post:

Shape isn’t everything, but it’s one tool to help provide differentiation and uniqueness in icons. But not anymore.

Just the mere silhouette of the old Keynote icon is more recognizable, and thus more iconic, than any icon on any platform from Apple today.

No civil engineer would ever suggest changing yield and stop signs from their iconic triangles and octagons to identical squircles. The human visual system evolved to be remarkably good and quick at identifying shapes. The primary element of an app icon is the semantic meaning of its illustration. Color and shape are secondary. With the squircle mandate, Apple has removed shape from the equation.¹ The purpose of icons is right there in their name: to be iconic. Shape was often the most iconic thing about an icon. Now it’s no part at all.

It makes no more sense than removing color. But Apple did that too! One of the purported reasons for the new icon guidelines across MacOS and iOS are the tinted and clear appearance options introduced last year with Liquid Glass and the OS 26 releases. These are both terrible ideas that remove color as a distinguishing factor, reducing ostensibly distinguishable icons into indistinguishable buttons. Adam Engst skewered the Clear and Tinted icon appearance options in a recent column at TidBITS, and ran a poll to see if anyone actually used them. Spoiler: nope.

App icons used to be exuberantly fun and so beautiful that they were the subject of two splendid coffee table books. This squircle shit is no fun at all, and ugly as sin.

Let’s go back.

ChatGPT’s native Mac app, on the other hand, is a truly native Mac app. It looks like a Mac app and feels like a Mac app because it really is a Mac app. I’ve liked it ever since it launched back in May, and it keeps getting better. And I keep using it more and more as my go-to resource for answering questions.

I asked Claude, “What is the best way to engineer a native Mac app? What frameworks and developer tools should one use if the goal is a great Mac experience?” Claude’s answer started by positing it as a decision between SwiftUI and AppKit. Perhaps Anthropic’s Mac engineers should have asked Claude this same question before they built this turd of an Electron app.

In March of this year, linking to Anthropic’s announcement that Claude Code and Claude Cowork can take control of your Mac to accomplish agentic tasks, I returned to the same question:

The Claude Mac client itself remains a lazy Electron clunker. If Claude Code is so good I don’t get why they don’t prove it by using it to make an even halfway decent native Mac app.

I’m not the only one who has pondered this. Drew Breunig wrote “Why is Claude an Electron App?” in February this year:

On the surface, this ability should render Electron’s benefits obsolete! Rather than write one web app and ship it to each platform, we should write one spec and test suite and use coding agents to ship native code to each platform. If this ability is real and adopted, users get snappy, performant, native apps from small, focused teams serving a broad market.

But we’re still leaning on Electron. Even Anthropic, one of the leaders in AI coding tools, who keeps publishing flashy agentic coding achievements, still uses Electron in the Claude desktop app. And it’s a slow, buggy, and bloated app.

So why are we still using Electron and not embracing the agent-powered, spec driven development future?

For one thing, coding agents are really good at the first 90% of dev. But that last bit — nailing down all the edge cases and continuing support once it meets the real world — remains hard, tedious, and requires plenty of agent hand-holding. [...]

For now, Electron still makes sense. Coding agents are amazing. But the last mile of dev and the support surface area remains a real concern.

I’m with Breunig up until the point where he accepts coding agents struggling with the final 10 percent as a justification for choosing Electron to create a Mac app. Plenty of people — individuals and teams alike — are using Claude Code to create terrific new native Mac apps. Just among my friends, Glenn Fleishman, Lex Friedman, and Jason Snellman, have all in recent months used not just AI coding assistants in general, but Claude Code specifically, to create genuinely native Mac apps that meet their own personal high standards for Mac-assedness, forged through decades of literally professional Mac snobbery. A comprehensive catalog of Mac-assed apps made with the assistance of Claude Code, would, I suspect, be remarkably long.

The struggle with the last 10 percent is unrelated to AI coding. It’s the nature of all software engineering. There’s a well-known adage that Wikipedia names the “Ninety-Ninety Rule”, attributed to Tom Cargill of Bell Labs:

The first 90 percent of the code accounts for the first 90 percent of the development time. The remaining 10 percent of the code accounts for the other 90 percent of the development time.

Cargill’s mathematically humorous formulation resonates because it not only explains why the final 10 percent consumes half the time, but also why software projects tend to take twice as long as expected. This universal truth holds whether the code is human-written, AI-generated, or a mix of both.

Breunig gets closer to the truth in a postscript, linking to the Hacker News thread discussing his post. The top-rated comment in the HN thread is from Boris Cherny, who works at Anthropic on the Claude Code team. Cherny wrote:

Boris from the Claude Code team here.

Some of the engineers working on the app worked on Electron back in the day, so preferred building non-natively. It’s also a nice way to share code so we’re guaranteed that features across web and desktop have the same look and feel. Finally, Claude is great at it.

That said, engineering is all about tradeoffs and this may change in the future!

I would rephrase the guarantee that “features across web and desktop have the same look and feel” as guaranteeing that the Mac app is restrained by the limits of the web and cut off from the breadth of idiomatically native functionality provided by the Mac’s native frameworks. Electron guarantees that an app feels just as wrong on all platforms. But the more relevant tidbit is this sentence: “Some of the engineers working on the app worked on Electron back in the day, so preferred building non-natively.” So it’s not that Claude somehow prefers Electron, but that “some of the engineers” at Anthropic do.

Some is doing some heavy lifting there, given that “some of the engineers” includes Felix Rieseberg, currently Anthropic’s engineering lead for Claude Cowork and Claude Code Desktop, and previously engineering lead for the Claude apps for MacOS and Windows. Rieseberg didn’t merely “work on Electron back in the day”. He is one of the principal people responsible for creating Electron, and remains today one of three members of the Electron project’s Administrative Working Group that “oversees the entire governance and project”. He literally wrote the book on Electron.

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. Windows uses Philips head screws, Linux uses hex screws, and MacOS requires Torx (of course) — but a hammer works the same way with all screws. That’s Electron. That’s Rieseberg’s baby.

Rieseberg, it turns out, hasn’t only had a hand in Claude being an Electron app. Per both his personal home page and LinkedIn profile, before joining Anthropic he spent over two years as the engineering manager for the desktop team at Notion, whose client for Mac is a massive 518 MB Electron app and a notoriously non-native experience.¹ Before Notion, Rieseberg spent 2016–2021 “as a Senior Staff Engineer and Engineering Manager at Slack, where I got to support a team of amazing C++ engineers building the cross-platform desktop framework Electron — as well as Slack’s desktop apps for macOS, Windows, and Linux.”²

Finding out that one guy — who is a senior Electron maintainer — has led the teams for the desktop clients for Slack, Notion, and now Claude is like discovering that it was one guy — whose family business was a distillery — who helmed the Titanic, piloted the Hindenburg, and then served as air traffic controller for Amelia Earhart.