2026-03-25 19:43:29
Look, let's try to be nice to Apple. They're a little slow on this whole "AI" thing. After spending years and years downplaying the role of the technology, most notably with several senior executives reported to have directly disparaged the whole "chatbot" movement as a passing fad, they're now playing catch up. Including, naturally, racing to build their own chatbot.
But those initial reports about how they would implement their upgrades to Siri indicated that there wouldn't be a stand-alone app for the service – again, that was undoubtedly too chatbot-like for Apple's taste – and instead it would be a system-wide integration, just like the current Siri. You know, Apple's "AI" system which has completely and utterly sucked for the past 15 years running.
Granted, Apple would be upgrading the technology powering Siri – going so far as to outsource the work largely to Google, their Big Tech frenemy which was also caught flat-footed in the early days of the current Age of AI. But their miss wasn't due to a lack of belief, but rather a corporate timidity and culture that they had to overcome. Which they seemingly now have. As such, they're right there in the thick of the AI race, miles – no, lightyears – ahead of Apple. So it was obviously wise of Apple to partner with one of the leaders in AI to give Siri a brain transplant. It was there own way to jump back into the race, at least from a product-perspective.
Just one little problem. The product itself.
Again, all the reports (and previous work) on Siri indicated it would remain this nebulous AI thing running in the background. But that's just not the way people are now trained – from the get go – to interact with AI. Much to the chagrin of Craig Federighi (now leading up Apple's AI efforts) and John Giannandrea (now since "retired" from Apple's AI efforts), the chatbot won.
But as Meta, Google, and others have learned, it's not enough to have a chatbot that resides amorphously everywhere. Users needs a centralized place to go to use AI. At least for now, in these early days. Which is to say, there needs to be an app.
You might have thought the company most synonymous with apps would have understood this from the get-go. But again, all indications were that they did not. They were clearly going to have to learn the hard way, a likely mistake that I noted over and over and over again. But I'll highlight what I wrote all the way back in June 2024, right after Apple unveiled Apple Intelligence:
The one thing I still wonder/think about post-WWDC is if Apple does still have a go-forward plan on the chance that the chatbot paradigm isn't just a fad. I'm using "chatbot" as a catch-all here – I also believe chatbots are a feature – but it's more about the overall interaction paradigm. That is, what if ChatGPT has taught a new generation that the best way to interact with AI is to ask "it" something (be it via text, voice, images, etc) and get something back – not just from your content, but from beyond. Apple doesn't currently have a way to do that – aside from the ChatGPT fallback. What if Apple needs to answer this call still?
Logically, this would be through Siri – assuming they can get Siri up to snuff, which is still a big assumption. And maybe we get to the point where "she" merges with Spotlight? And then Apple could just swap-out ChatGPT/Gemini/Claude/etc with their own LLM output. But the brilliance of their model here is that they can do this slowly and subtly over time. This doesn't have to be a rip-out Google Maps and shove a wonky Apple Maps in users' faces situation. The query routing system Apple has built should allow them to just slot in their own results as they're confident in them.
Or perhaps they do decide that this is just like the web search paradigm. In that case, they strike a deal with one of these players to be the default chatbot in exchange for a handsome fee and/or revenue split.
Well, it's happening. (Right down to striking those deals.) And it didn't even require getting it wrong (again) in iOS 27 before inevitably doing it correctly in iOS 28! Here's Mark Gurman reporting for Bloomberg:
As part of the shift toward this approach, Apple is testing a dedicated Siri app for the iPhone, iPad and Mac later this year. It rivals outside AI tools while also giving users a central place to access their past interactions.
Yeah, so just like every other AI service. Thank you.
But perhaps the most wild element of this report is that Gurman has either seen the new app or been in touch with someone who has and can describe it in great detail. (The leaks he's able to pull out of Apple remain increasingly wild to me.)
The app’s main interface will display prior conversations in either a list or a grid of rounded rectangles with text previews. Users can pin favorite chats, save older conversations, search across interactions and start new chats via a prominent plus button.
The conversation view resembles a thread in Apple’s Messages app, with chat bubbles and a text entry field. It also includes a toggle for switching in and out of voice mode and an option to upload attachments — such as documents and photos — for analysis. These features have already become standard in modern chatbot interfaces.
When starting a new conversation, Siri will offer suggested prompts based on prior usage. The interface adapts to light and dark modes, with a white background and dark text or the inverse.
Again, all of that sounds good/standard. And amazingly, he goes even more in-depth on the UI Apple is clearly at least testing:
Users will still be able to trigger Siri via the power button or voice command, but Apple is testing a redesigned interface that replaces the glowing edges effect introduced in iOS 18.
One new design in testing places Siri at the top of the screen within the Dynamic Island, the mini-interface that Apple introduced in 2022. After it’s activated, Siri will prompt the user to “Search or Ask.”
When processing a request, a pill-shaped indicator labeled “Searching” appears, alongside a glowing Siri icon. Once results are ready, the interface expands into a larger translucent panel with Apple’s Liquid Glass design. Users can pull the menu down further to begin conversing back and forth.
This points to the stuff that other AI apps/services can't do because they don't control the iPhone, Apple does. Again, Apple went about this at first all wrong because the chatbot interface won, but being able to do both will likely be pretty killer here. I "hack" this together by using the iPhone "Action Button" to invoke ChatGPT, but it just launches the app, it's not as seamless as, say, hitting a button and talking to Siri.1 Assuming Siri actually works now – thanks, Google – we could be getting the best of both worlds from Apple. And that could actually push the AI interaction paradigm forward. Beyond the chatbot!
This points directly to Apple's potential power here. Yes, in AI. Yes, despite years of missteps and setbacks. If they can come in now with an actually working Siri – I know, I know! – in both app and system-wide form, they could actually vault right back to the top of the AI conversation.
The other players are all working on hardware to try to counter the hold Apple has with the iPhone. But they're not going to replace the iPhone – at least not anytime soon, so... Again, there's a world in which Apple, despite the endless wandering through the AI desert, spending basically nothing on CapEx while their peers spend hundreds of billions, wins. Again.
The bigger issue remains that if by outsourcing the core work to Google, Apple never is able to catch up from a pure technology stand-point and this encumbers the true "what's next" shift in hardware. But again, that's likely years away. The hope would be that Apple is simply buying themselves more time to meet that moment as well. I'm more skeptical of that longer term if AI really does change everything, which is why I don't think it's completely insane to try to buy Anthropic right now. (It's just mostly insane.)
Anyway, it all starts with getting Siri right. And that includes implementing Siri right. And that means there needs to be an app for that.
One more thing: Back to Gurman's report:
Apple is also working to replace its existing on-device search system, Spotlight, with Siri. The new unified interface helps users find local content or submit broader queries in one place.
Yes, this obviously needs to happen. Per my point two years ago, Siri and Spotlight should merge into the one search to rule them all.
I don't know about the reported "Search or Ask" functionality per above – sounds sort of like the 'Dr. Know' system from the movie actually called A.I. which confuses the user. In this case, an AI android. "Flat fact?"
1 You can sort of "hack" this together too thanks to Apple's Shortcuts app, but it's still a bit more wonky than a true system-level integration. ↩
2026-03-24 22:19:32
The opening is almost like the beginning of the music video for U2's "Where the Streets Have No Name". Just about a minute in, we see him getting mic'd up, ready to take the outdoor stage. Not Bono. Steve Jobs.
The year is 1999. There is no black turtle neck, but rather a gray long-sleeve tee. The jeans are ripped in a very 1990s way. The music fades as Jobs walks up, looking a bit tired but healthy. He is just 44 years old.1
Yes, a new video of Jobs has been unearthed. And yes, it simply must be written about. This is the way.
And it seems like perfect timing for this video to surface given that Apple has just unveiled the MacBook Neo – the first laptop to come in fun colors since the candy-colored iBooks back in the day. This video is that day. The setting is 1 Infinite Loop – Apple's main HQ before the spaceship landed – and it's a breezy day in July 1999. Jobs and a lot of the team has just returned from New York where they used Macworld to unveil the consumer laptop. Notably, the final piece of the puzzle Jobs laid out when he returned two years prior to the company he founded.
Yes, the quadrant was now complete.
Jobs clearly felt great about the unveiling. "Everyone is going nuts – including our competitors," he said to laughs. Again, it sounds a lot like today.
He goes on and on about how "awesome" the iBook is – especially since it had to follow the iMac, an incredibly tough act to follow. And while others had struggled to do consumer portables well because of all the corners that need to be cut in order to make such devices affordable Jobs believed Apple nailed it and seemingly couldn't help but grab one to show it off, just like he would in a normal keynote.
Speaking of, he told the crowd of employees about his favorite moment in his presentation when he was able to walk around with the iBook, surfing the web. As he told it, everyone was trying to figure out what was going on. "And then we told them about AirPort."
It's nearly impossible to think about now, but in 1999, wireless internet was not ubiquitous. So this must have seemed like pure magic. And Jobs describes how they were able to make this work on a consumer device thanks to some technology from Lucent – which Jobs noted that Apple was able to "extract" out of their labs.
The resulting AirPort product was something Jobs was clearly proud of. "It just works." Hearing such praise now, it's especially wild to me that Apple was so quick to kill the product off a decade ago – which I wrote about at the time as their "ErrorPort" moment.
Steve Jobs, famously, didn't like to look back. But he also clearly recognized the moment here, two years after returning to the company, with Apple having just completed that all-important quadrant.
"You've completely overhauled Apple," he beams to his employees.
With the iBook in place, completing their original deceptively "simple" plan, Jobs notes that they can now enter a mode where they're turning over those four key products as fast as they can to stay ahead of the competition. The same basic strategy Apple has today, of course. Albeit with a product lineup not quite so simple.
But Apple was a very different company in 1999. This was a couple years before the iPod, so all that mattered was moving Macs. Jobs noted that Apple was selling about 4 to 5 million computers a year. Last year, Apple likely shipped just north of 25 million Macs. And about 75 million iPads. And maybe another 250 million iPhones.
Jobs pulled out a piece of paper to close with "one last thing":
"A lot of people have declared our turnaround officially complete. And you would have to say that’s true. We’ve had seven consecutive profitable quarters. We made $200M last quarter. That’s a lot of money! And we’ve got great products. But, you know, I never looked at it that way. The reason I came here had nothing to do with turning Apple around. Because that’s about the company. And I know we all love this company, but what we love even more is putting these great products out into the world and seeing people use them. And so the reason I came back here. And I’m sure the reason you’re here isn’t to turn Apple around, it’s to make Apple great again. Right? And I think we now have that possibility. We now have that possibility with the work you’ve all done in the last two years. The foundation we have now is really great."
This is a great message delivered in a very Jobsian way: this wasn't about a turnaround, this was about putting great products into the world. The turnaround was a byproduct of that.
Oh and did you catch it? Yes, Steve Jobs may have invented "MAGA" before anyone in Donald Trump's orbit did. Make Apple Great Again.
Jobs went on to note that the real secret to Apple's success is that they're the last company willing to "make the whole widget". And because they don't have to constantly convince endless partners to do the work they believe will make for great products, they have a unique advantage over the Dells and Compaqs of the world. Even yes, Microsoft.
Talking about their wireless breakthroughs, Jobs noted that the PC guys simply couldn't do it even though the technology has been there for the taking. But when Dell or Compaq go to Microsoft to get the software to make it all work, they'll get: "Well, it’s not high volume. We’ve got 38 million things wrong with our software. We’ll put it at the bottom of the list." This drew huge laughs from the audience.
Nothing beats a shot at Apple and Jobs' old foe.
"We can break through those things and bring innovation to customers because we’re the last people in this business that give a shit about making great computers."
Finally, Jobs spoke to focusing on Apple's core markets with creative professionals, consumers, and education. He lamented how Apple has slipped a bit in the latter market and wanted Apple to renew focus. Which seemingly worked for a time, before focus was lost again – only to be regained again with the MacBook Neo! It all comes back around...
"I happen to know all the things in the pipeline. And I can tell there are so many more great things coming. It’s unbelievable. The products are just unbelievable. The best stuff i’ve ever seen in my life. So I think we’re really gonna be able to rock and roll the next few years."
Indeed, they did.
1 Holy shit, I realized when doing the math that Jobs in this video is almost the exact same age that I am right now. That's sort of wild to think about... ↩
2026-03-24 03:55:13
It goes without saying that Meta has a great business. One of the greatest ever created, in fact. At the same time, it's almost entirely a one-dimensional business. The social networks have changed, but the monetization remains the same. Ads.
I'm perhaps even being generous with "almost" here. Meta's business last year was roughly 98% advertising.
To be fair, in the success state, this ends up being the knock on most companies that are able to crack their business model. And again, few have cracked it as well as Meta has. And AI will likely help them crack it further. Still, it's an incredible amount of concentration for a company that is 22 years old. And has been publicly traded for 16 of those years...
2026-03-21 22:48:40
Anyone complaining about the latest coat of paint on top of macOS should stop and read this post by Ed Bott. Or this one. Or this one. Or any of these. But Bott in particular eviscerates Microsoft this week for their (mis)management of Windows.
Granted, it has been a long time since I used Windows on a regular basis. While it dominated the first 20 years of my computing life (post-MS DOS), the last 20 years have been almost entirely on macOS (post-OS X). So I guess I didn't realize just how bad Windows 11 apparently is. Maybe not a Vista-level disaster,1 but judging from Microsoft's own post about their (apparently newfound) "commitment to quality", it sure reads like basically everything in Windows 11 well, sucks.
Here's Bott commenting on that post:
What's most remarkable about this post is what it doesn't contain. Here's how Davuluri kicked things off:
"Every day, we hear from the community about how you experience Windows. And over the past several months, the team and I have spent a great deal of time analyzing your feedback. What came through was the voice of people who care deeply about Windows and want it to be better."
That paragraph belongs in the non-apology Hall of Fame, with a cross-reference to "Friday news dump" – a classic PR technique that aims to minimize media coverage of the awkward news being released.
When I read that paragraph, I was gobsmacked. They "spent months analyzing feedback"? Seriously? They needed charts and graphs to figure out that people just want Windows to work?
The laundry list of changes really does read almost as if it would be easier to throw the entire OS out and just start over – by doing exactly the opposite of what has been done to date.
These are complaints that have been going on for years, and have seemingly grown in-step as Microsoft slowly forced Windows 11 upon the majority of their user base. That is, the only reason everyone wasn't complaining on day one is simply because most of them chose to stay on Windows 10. Once they upgrade, the complaints start.
Again, this sounds somewhat similar to macOS Tahoe on the surface. But again, it's just that: the surface. Most of the complaints there are superficial, ranging from icon design to transparency settings. Yes, most of it stems from the "Liquid Glass" updates, which were clearly conceived for iOS, but also brought to the Mac in an attempt to unify the design language. But this seems quite different from the situation with Windows, where some pretty fundamental elements of the OS just seem broken or buggy or worse.
Sure, we're in the post-Windows era of Microsoft, but still, there are billions of users of that OS on a daily basis. Microsoft may no longer really care about that user base as it's no longer the primary driver for the company, but still... it's wild that they would let Windows degrade in such a way. These list of changes almost read as if no one inside of Microsoft actually uses Windows any more.
But really, the complaints read mostly like: just give us the old Windows back. And sure, people generally hate change, we know that. But they seem to especially hate it when you're shoving constant updates and notifications (or worse) in their face to try to upsell them on whatever initiative Microsoft does care about right now. This is clearly a "milking the base" situation. And when you're spending well over a hundred billion dollars a year to build out your future in AI, that Windows user base must look like the world's largest herd of cows. Back to Bott:
As I noted earlier this year, Microsoft has been relentlessly shoehorning AI features into places where they absolutely don't belong. I follow feedback in forums carefully, and I would estimate that roughly 99% of the comments about AI features boil down to a simple request: Please stop.
In a blog post welcoming 2026, CEO Satya Nadella argued that "we need to get beyond the arguments of slop vs. sophistication." In response, the internet made "Microslop" the most popular meme of the new year.
Bowing to that feedback, Microsoft now says it is backing off. "You will see us be more intentional about how and where Copilot integrates across Windows, focusing on experiences that are genuinely useful and well‑crafted," Davuluri says. Specifically: "We are reducing unnecessary Copilot entry points, starting with apps like Snipping Tool, Photos, Widgets, and Notepad."
Copilot is clearly a mess for Microsoft on a few fronts, hence why they're loading up the cockpit with even more copilots (while perhaps shoving the captain out with the most golden of parachutes). But Microsoft obviously thought that AI would be the future of Windows. And they seemingly had an opening there given their prescient early bet on OpenAI. Then it all went to shit. Now they have to rip that shit out of Windows, lest that user base start jumping out...
Speaking of, the timing here does seem more interesting than a typical Friday news dump. Apple, of course, just unveiled the MacBook Neo. Their $599 computer is priced to move. And a lot of that movement will likely be first-time Mac buyers – as is clearly already the case. Those users probably aren't coming from Linux. And a large subset of them probably aren't coming from anywhere – but they are undoubtedly would-be PC (or Chromebook) buyers for school. That, of course is not good news for Microsoft. But it's perhaps especially not good news when you have an OS that your current user base hates.
Is $599 a pricey fix for Windows 11? No doubt. But it's almost a permanent one.
One that goes far beyond Steve Jobs' famous "glass of ice water in hell". This isn't one good piece of software installed in a burning sea of lava, this is extinguishing the fiery hell pit with the arctic ocean that is macOS. Well, provided you can live with Liquid Glass. Which pretty much any Windows user would gladly take over this situation at this point, one suspects.
Microsoft took Windows to 11. Perhaps they should have stayed at 10.
M.G. Siegler
M.G. Siegler
M.G. Siegler
1 Looking back, it seems almost as if Microsoft is locked into a situation where nearly every other version of Windows is a dud. It's sort of like the thing where only every other Star Trek movie would be good. With Microsoft, it feels like every time they try to branch out a bit, they mess up Windows to the point where they have to course correct, mainly by backtracking on the bigger changes. ↩
2026-03-20 20:33:05
The year is 2014. Amazon, realizing that the world has almost entirely shifted to smartphones for their computing needs, felt left out. They were early to the newfangled gadget race with the Kindle. And dipped their toes in the tablet waters with the Kindle Fire in 2011.1 But now, directed by Jeff Bezos himself, it was time for Amazon to go for it. The Fire Phone was a big swing. And miss. In part because no one would tell Bezos "no". But in part because Amazon was just far too late.
The year is 2026...
The latest effort, known internally as “Transformer,” is being developed within its devices and services unit, according to four people familiar with the matter. The phone is seen as a potential mobile personalization device that can sync with home voice assistant Alexa and serve as a conduit to Amazon customers throughout the day, the people said.
Bezos may be gone,2 but history repeats...
As envisioned, the new phone’s personalization features would make buying from Amazon.com, watching Prime Video, listening to Prime Music or ordering food from partners like Grubhub easier than ever, the people said. They asked for anonymity because they were not authorized to discuss internal matters.
Come on, there is no way anyone needs that device. These needs were covered 12 years ago. They're more covered now – still by Apple and Google. BUT...
A key focus of the Transformer project has been integrating artificial intelligence capabilities into the device, the people said. That could eliminate the need for traditional app stores, which require downloading and registering for applications before they can be used.
Alexa would likely be a core feature but not necessarily the primary operating system of the phone, the people said.
I'm going to zag a bit here in thinking that this may not be totally insane.Silly 3D screen gimmicks may not have been enough to get people to switch phones but there is a world in which AI can. We're not quite in that world yet. But we're perhaps closing in on it. And this Amazon project sounds pretty early.
A month ago, I made the case that despite the endless consternation about Apple's place in the Age of AI, they may actually end up positioned well thanks to one thing: the iPhone. First and foremost, there's certainly a case to be made that the best device for AI is the one you use most often. And that's the iPhone. Second, all the newfangled devices in the works being built around AI – including by Apple – are undoubtedly going to rely upon the iPhone as their main hub for the foreseeable future. Why? That's where the connection is.
And again, it's the device you already have on you. Even OpenAI knows that you're unlikely to give that up, no matter how good any new AI device may be – even if it's one made by the guy who designed the iPhone! Sure, everyone learned from the lesson which Humane (a startup in which Sam Altman was the largest investor, mind you) learned the hard way. But they also learned from said Fire Phone.
But again, what if there is an opening here? While everyone else, including Meta, is conceding to Apple's position at the moment, what if it is a time to try to re-enter the phone business? With a device completely rebuilt for AI? I'm not saying it will work. In fact, there's a very good chance it won't – least of which because aside from the product itself, competing in the phone business is insanely hard for a number of other more logistical reasons. But it may be worth a shot? Especially if you're in the midst of spending, say, $200B this year on AI infrastructure? Why not throw a few billion at an AI phone project?
And Amazon has a potentially interesting guy to do it. Last May, I noted what seemed to be Amazon's attempt to jump into the new AI device race, with the 'ZeroOne' project. And that was being led by J Allard, a name which long ago dropped off the radar, but those of us around long enough will remember well from the original Xbox days and later the Zune at Microsoft. The ZunePhone never happened – nor did the ill-fated "Courier" project – but might Allard be able to get to take his swing under the guidance of his old Microsoft compatriot Panos Panay?
Again, it all sounds pretty early. To this point:
Three people who have worked on the Transformer project said the phone is still under development. The company has explored both a traditional smartphone and a so‑called “dumbphone” with more limited features that could help counter screen addiction. Amazon has not yet sought wireless carrier partners for the device, these people said.
One inspiration for the new phone has been the Light Phone, two of the people said, a $700 minimalist smartphone with a camera, map, calendar and not much else, such as an app store or web browser.
A dumbphone or feature phone could also help Amazon market it as a potential second handset to accompany iPhones and Samsung Galaxies already in customers’ pockets, the people said. Such handsets, like the Light Phone and flip phones, accounted for 15% of global handset sales in 2025, according to Counterpoint Research.
Certainly the positioning as a "second device" would be the safer path for Amazon to attempt here. But I'm not certain they shouldn't try to go for the big dogs. Especially given Apple's clear vulnerability in AI. To that end, and given Zuck's intense hatred of being beholden to Apple, I'm sort of shocked Meta hasn't been working on a new Facebook Phone!3
I would also just note that Amazon not only has their huge investment in Anthropic, but is pulling OpenAI a lot closer. What if OpenAI's new device didn't need to pair with the iPhone, but with an Amazon phone instead? And what if some combination of Claude, ChatGPT, and Alexa could power Amazon's device? A true Anyone-But-Google AI Alliance!
I will end by noting what I closed with just about a year ago:
Beyond the AI moment, all of this movement also seems tied to the fact that the iPhone – and smartphones in general – are starting to feel a bit long in the tooth. People are perhaps primed for that "what's next". Which is a billion times easier said than done, of course. But Allard has a good pedigree – even the Zune, which we all make fun of now, was a pretty good device and ahead of its time in ways. It just tried to fast-follow the iPod without a lot of Apple's built-in strengths in consumer. And it came in brown.
Could be worse. Could have been the Fire Phone. Let's not do that again, Amazon.
Or maybe let's?
M.G. Siegler
M.G. Siegler
M.G. Siegler
1 A story I broke way back when! ↩
2 Well, from day-to-day operations, but he's still chairman of the board, of course. Not to mention the largest shareholder... ↩
3 Yes, another failed attempt to compete back in the day. It would obviously need a new name now... MetaPhone? ↩
2026-03-20 01:59:43
"We cannot miss this moment because we are distracted by side quests." Begun, the Fidji Simo era of OpenAI truly has?
Ever since she was hired last May, my read – and I believe the read of many – was that there was a reason they gave her that secondary CEO title. I mean, it may have taken that to convince her to take the role, but it also perhaps pointed to what the actual role would be. That is: the CEO in all but name. But actually, with the name too.
As with all things OpenAI, it's complicated...
