How Apple missed and still hasn’t cracked AI

Apple CEO Tim Cook
Apple’s foray into generative artificial intelligence (GenAI) with its Apple Intelligence vaporware and a promised-but-not-delivered Siri upgrade has floundered badly. Heralded in Apple ads as a game-changer, the initiative has faced criticism for underwhelming performance, limited functionality, and a failure to catch up to, much less keep pace, with competitors like xAI’s Grok, OpenAI, or even Google’s Gemini. Bloomberg Businessweek‘s in-depth analysis uncovers the internal challenges, strategic errors, and market pressures that have left a clearly visionless Apple scrambling in GenAI, raising questions about the company’s ability to compete in the rapidly evolving AI landscape.
Mark Gurman and Drake Bennett for Bloomberg Businessweek:
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Back in 2018 it looked like Apple Inc.’s artificial intelligence efforts were finally getting on track. Early that year, Craig Federighi, Apple’s software chief, gathered his senior staff and announced a blockbuster hire: The company had just poached John Giannandrea from Google to be its head of AI. JG, as he’s known in the industry, had been running Google’s search and AI groups… To Apple’s leadership, the Giannandrea hire wasn’t just a coup at the expense of their fiercest rival. It was also, they hoped, the start of the company’s transformation into an AI powerhouse. Just before the death of co-founder Steve Jobs in 2011, Apple had unveiled its voice assistant, Siri. At first, Siri felt like something out of science fiction—once again, Apple had taken a futuristic computing concept and turned it into a mainstream product. But within a few years, Google, Amazon.com Inc. and other competitors had introduced voice assistants that felt far more advanced, while Apple’s struggled with basic comprehension and commands.

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MacDailyNews Take: It’d be genius on Google’s part if Giannandrea were a plant: “Yeah, John, we’re okay here now. We have the people we need in place. Take a bunch of Apple’s money, go over there and do a whole lot of nothing. Screw ’em hard, John!”

Federighi’s excitement in announcing the hire was palpable—Siri had been handed off multiple times since its launch, ending up with him, and now he was passing it off to Giannandrea. “This is exactly the kind of person we needed for AI,” he told his staff. In addition to Giannandrea’s work at Google, where many considered him the most powerful executive except the CEO, he’d been chief technology officer of internet pioneer Netscape. “Who else in the world would you get?” asks someone involved in the hire.
Seven years after Giannandrea arrived, the optimism he brought with him is gone. Apple’s AI has only fallen further behind.

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MacDailyNews Take: Seriously, it’d be genius. Cripple Apple from within. Feckless Cook had already proven multiple times to be unable to make successful high-profile hires. Just add Giannandrea the growing list. Apple would never be able to prove he was a plant.

Apple, like its competitors, has rolled out new AI features, but they’ve mostly been notable for being delayed and underwhelming. Last June, at its Worldwide Developers Conference (WWDC), the company announced Apple Intelligence… The prospect of truly AI-powered devices led Apple’s share price to rise sharply. The buzz grew in September, when the company announced that its newest phone, the iPhone 16, had been “built from the ground up” for Apple Intelligence. But when the device went on sale that month, it didn’t have the AI features…
As for the Siri upgrade, Apple was targeting April 2025, according to people working on the technology… The planned rollout was delayed until May and then indefinitely, even as the features were still being promoted on commercials for the iPhone 16. Some customers who’d bought what they thought would be AI-enabled devices joined class-action lawsuits accusing Apple of false advertising.

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MacDailyNews Take: As we wrote in March, “False advertising is false advertising. Even Tim Cook’s wheezing vaporware factory – or, more likely, its lawyers – can figure that out. Class action lawsuits by iPhone 16 buyers to commence in 3, 2…”
The Apple Intelligence vaporware [is] false advertising, fraud, and lies. Those will be the basis for class action lawsuits from iPhone, iPad, and Mac customers soon enough. And Apple will deserve them all. MacDailyNews, March 14, 2025
See also: Apple sued for false advertising over Apple Intelligence – March 21, 2025

The new Siri won’t be out in time for next month’s WWDC, a year after the upgrade was first announced… “This is a crisis,” says a senior member of Apple’s AI team. A different team member compares the effort to a foundering ship: “It’s been sinking for a long time.” According to internal data described to Bloomberg Businessweek, the company’s technology remains years behind the competition’s.

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MacDailyNews Take: You cannot be ahead of the competition when, instead of a visionary, you have an operations manager as CEO – whose main claim to fame was/is exploiting cheap Chinese labor in order to generate huge margins – endlessly iterating Steve Jobs’ innovations for well over a decade.
We shall see, but it’s likely that Apple will do the same thing [with Cook] they did with Jony Ive – give him a transition title with nothing much to actually do in order to assuage Wall Street (and as they also just did with [CFO Luca] Maestri) when Cook finally decides to bow out — which he should have done long ago after serving 3-5 years following Steve Jobs’ untimely demise; a caretaker CEO hanging on well over a decade leads to missing paradigm shifts like GenAI and having to execute vaporware schemes in order to try to catch up. Until Apple again gets a visionary CEO, these issues will compound. It would also be nice to get a charismatic CEO who can handle live keynotes again. – MacDailyNews, July 27, 2024

What’s notable about artificial intelligence is that Apple has devoted considerable resources to the technology and has little to show for it. The company has long had far fewer AI-focused employees than its competitors, according to executives at Apple and elsewhere. It’s also acquired fewer of the pricey graphics processing units (GPUs) necessary to train and run LLMs than competitors have. Its leadership has undergone a significant shake-up this year, in response to these and other issues, with Siri and other AI-related teams removed from Giannandrea’s command.

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MacDailyNews Take: As usual, you read it all here first:
Apple pays and has been paying John Giannandrea, Senior Vice President of Machine Learning and AI Strategy, millions upon millions of dollars for years. WTF of any import does he really do? WTF of any import has he really delivered? Have you used Siri lately? Yup, it’s still a steaming pile of dogshit.
Where’s Apple’s generative AI, John? “Too hard; too late; look for partners; gimme my paycheck and stock options.”
AAPL shareholders need to start asking real questions of these executives, especially those who are supposedly in charge of Apple’s “AI Strategy,” when the company clearly has none. How about some accountability for once? – MacDailyNews, March 18, 2024

But while some employees attribute the struggles to decisions made by particular executives, others see symptoms of a deeper problem… The company killed its self-driving car project last year, after spending billions of dollars on it across a decade, in part because it realized its AI wouldn’t be able to deliver on the promise of a fully autonomous vehicle. Continued failure on AI would likely doom many of Apple’s plans for the future, from augmented-reality glasses and robots to watches and earbuds that can recognize objects in the world around them. And it would leave Apple at a grave disadvantage in the battle over how users will interact with smart devices in the coming years.
Eddy Cue, Apple’s senior vice president for services and a close confidant of Cook’s, has told colleagues that the company’s position atop the tech world is at risk.

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MacDailyNews Take: Again:
What’s wrong with Apple is that Tim Cook should have bowed out 3-5 years after providing continuity for the company as a caretaker CEO after Steve Jobs’ untimely death, not hung on, endlessly pumping out annual iterations of Steve Jobs’ innovations… burning tens of billions on failed projects (Scrapped Apple Car ‘a massive disappointment that will alter the course of the company’s history, perhaps for decades to come’ – Gurman, March 11, 2024) and releasing a half-baked DevKit as a consumer product in order to cover for his glaring lack of vision (The Apple Vision Pro is ‘expensive, impractical, and clearly nowhere near ready for the mass market’ – Benedict Evans, March 22, 2024). – MacDailyNews, April 11, 2025
You can keep blaming Cooks’ bad hires, but things won’t meaningfully change until Apple corrects the source of its issues. Where does the buck really stop at Apple Inc.?

Still, when Jobs first encountered Siri — originally an offering in Apple’s App Store — he was hooked… Jobs immediately saw it as far more than a mere app — he believed it could potentially become the primary user interface for Apple’s devices… Jobs turned Siri into one of Apple’s top development priorities. “He made it his personal project,” [Siri co-creator, Dag] Kittlaus remembers. “I met with him every week until he no longer could for health reasons.” … [T]he company was blindsided by ChatGPT’s launch in November 2022. One senior executive says Apple Intelligence “wasn’t even an idea” before that. “It’s not like what OpenAI was doing was a secret,” says another. “Anyone who was paying attention to the market there should have seen it and jumped all over it.”
Apple’s Siri plans were even further behind. The company had been promoting the assistant’s new features in TV ads since the iPhone 16 launch, despite their being nowhere near ready… In March 2025, Apple confirmed a Bloomberg News report that the new Siri would be postponed… The following week, the Siri team’s then-boss, Senior Director Robby Walker, met with his demoralized workers for a kind of pep talk… Walker told everyone at the meeting to develop the upgrades for the next version of the iPhone operating system, iOS 19, due in September. But he also told them he wasn’t sure when the upgrades, which didn’t work properly a third of the time, would actually be released, in part because other features were a higher priority… Members of the Siri group say Walker’s assessment actually understated the problems… With the project flagging, morale on the engineering team has been low. “We’re not even being told what’s happening or why,” one member says. “There’s no leadership.”
This spring, Giannandrea was stripped of all control over product development, including the programs for Siri engineering and future robotics devices. That came after Cook lost faith in his ability to execute the creation of new products, according to fellow executives. Siri is now headed by Mike Rockwell, who led the team that created the Vision Pro mixed-reality headset.

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MacDailyNews Take: Which has sold fewer than 450,000 units total, but which is reportedly excellent at generating regret: Early adopters of Apple’s $3,500 Vision Pro headset express regret – The Wall Street Journal, May 15, 2025
That said, Rockwell is, and has long been, an advocate for Siri and it was Cook, not Rockwell, who pulled the trigger way too early on releasing Vision Pro, so fingers crossed.
One thing Apple should definitely consider is killing off the Siri name and all of the negative baggage it carries.
With Siri now basically holding a full house of negative associations built up over years of neglect, incompetence, and empty promises, perhaps, if Apple actually manages to fix Siri this time around (a big IF; we’ve heard it all before), a rebrand might be useful. Kill off Siri and introduce something new – since it will actually finally be new – in order to allow it to take off on its own without the weighty baggage of the Siri name. – MacDailyNews, April 22, 2025

I bought a new iPhone for Siri with Apple Intelligence and all I got was this lousy glow. pic.twitter.com/I0G4Wxf5Im
— MacDailyNews (@MacDailyNews) March 25, 2025

Rockwell reports to [Craig] Federighi, who’s taken on more responsibility for Apple’s AI software-related product road map…
Federighi, Apple’s software chief, remained reluctant to make large investments in AI — he didn’t see it as a core capability for personal computers or mobile devices and didn’t want to siphon resources away from developing annual updates to the iPhone, Mac and iPad operating systems, according to several colleagues. “Craig is just not the kind of guy who says, ‘Hey, we need to do this big thing that will require big budgets and a ton more people,’” a longtime Apple executive says…
Giannandrea’s product managers have been moved under Federighi’s oversight, while Rockwell has revamped the Siri management team by putting his top lieutenants from the headset project in charge. Walker, who’d been running Siri under Giannandrea, lost most of his engineers and was assigned to a new project.

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MacDailyNews Take: All of the deck chairs are being rearranged except for the one that really matters.

Apple’s long-standing commitment to user privacy also hindered it. The company’s base of 2.35 billion active devices gives it access to more data — web searches, personal interests, communications and more — than many of its competitors. But Apple is much stricter than Google, Meta and OpenAI about allowing its AI researchers access to customer data… “There are a thousand noes for everything in this area, and you have to fight through the privacy police to get anything done,” says a person familiar with Apple’s AI and software development work. An executive who takes a similar view says, “Look at Grok from X — they’re going to keep getting better because they have all the X data. What’s Apple going to train on?”

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MacDailyNews Take: As we wrote in February 2019, “About user privacy, most investors and analysts don’t seem to care, nor do, sadly, billions of consumers… Apple CEO Tim Cook might be futilely trying to sell something that nobody’s buying.”
We’re interested to see if Apple can really capitalize on their commitment to privacy or if it’ll take a major breach to wake up the majority of people or if even that would be enough to make privacy a real selling point. Given how many gullible and/or ignorant people are willing to hand over their personal data for free to the likes of Google and Facebook (while mailing their DNA to other companies, no less), we’re not seeing Apple’s devotion to privacy as very salable. — MacDailyNews, March 19, 2018
Privacy is important and it’s a selling point to us, but Apple needs to figure out a way to safeguard privacy while also making serious headway in GenAI – and quickly.
Doing a deal with Elon Musk – to use Grok (among, if not the very best GenAI today) and/or access some portion of X.com data – would be smart, but we don’t see Cook being able to bring himself to do it due to personal politics (which is yet another way Cook handicaps the company by limiting its appeal to the widest possible audience; a dereliction of his fiduciary duty to shareholders).
The more AI plugins available to Apple Intelligence users at the system level, the better. While Google’s Gemini is perhaps the last AI we’d ever choose (or second to last, after Meta’s) due to privacy, bias, and other issues, the more options the better until or unless Apple can catch up and provide its own quality GenAI. – MacDailyNews, April 30, 2025
We switched our main GenAI use from Google’s Genesis to Grok 2 months ago because it was clearly better in multiple ways, from summarizing text to generating images. Grok 3 beta, which we are now using, is clearly a major advance. – MacDailyNews, February 20, 2025

Giannandrea retains oversight of AI research, the development and improvement of large language models, the AI analysts, and some infrastructure teams. Insiders say that some Apple executives have discussed the idea of shrinking Giannandrea’s role still further or of him being put on a path to retirement (he’s 60), but that Federighi and others have concerns that if he leaves, the prized researchers and engineers he brought in would follow him out the door.
At least for now, Giannandrea is staying on, telling colleagues he doesn’t want to leave before the company’s AI work is in proper shape.
He’s also professed to them that he’s relieved Siri is now someone else’s problem…
Sources at Apple say that, for the next version of iOS, slated for introduction at WWDC 2025 in June, the company plans to focus on upgrading existing Apple Intelligence capabilities and adding some new ones, such as an AI-optimized battery management mode and a virtual health coach. Significant upgrades to Siri—including the ones promised nearly a year ago—are unlikely to be discussed much and are still months away from shipping. The Apple sources say the company, despite its hopes for LLM Siri, is also preparing to separate the Apple Intelligence brand from Siri in its marketing. It’s a tacit admission that the voice assistant’s poor reputation isn’t helping the company’s AI messaging. Another change: Apple, for the most part, will stop announcing features more than a few months before their official launch.

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MacDailyNews Take: Genius ideas.
With Siri now basically holding a full house of negative associations built up over years of neglect, incompetence, and empty promises, perhaps, if Apple actually manages to fix Siri this time around (a big IF; we’ve heard it all before), a rebrand might be useful. Kill off Siri and introduce something new – since it will actually finally be new – in order to allow it to take off on its own without the weighty baggage of the Siri name. – MacDailyNews, April 22, 2025
The further out you announce things, the more vaporware risk you assume. – MacDailyNews, October 10, 2019
Believe it or not, there’s EVEN MORE in the full article here.
Receipts:

Apple was caught flat-footed, due to a lack of vision on the part of leadership… So, the only solution is to partner with a [Google, OpenAI, Baidu, etc.] for the real GenAI stuff while pretending (marketing) really hard that some on-device AI Apple has whipped up in a few months is “insanely great Apple innovation” that’s at the heart of Apple’s 2024’s AI announcements when it’s really just an adjunct… Watch Apple make a big show of its on-device AI at WWDC and run many ads touting it from June onwards.
Apple hopes to buy time for the data center buildouts and investments that will be required for them to someday own their own AI technology and not have to license it from the likes of [Google, OpenAI, Baidu, etc.].
This is what happens after a decade plus with a caretaker CEO at the helm after he hits the last page of his iteration playbook, yet attempts to stay in the game for too long. – MacDailyNews, April 1, 2024

The new “AI features” for iOS, iPadOS, and MacOS to be revealed at WWDC is mainly a marketing exercise. The pressure is on Apple’s marketing team to position the company as an innovator in the space (“only Apple does so much on-device AI which enhances users’ privacy to ‘stunning’ effect,” etc.) that also makes “smart partnerships” with other AI companies (OpenAI, for example; even though it’s currently forced to partner if they want to offer any real GenAI features). Now, more than ever, finding themselves so far behind, Apple needs to sell, sell, sell! – MacDailyNews, May 28, 2024

When you're caught flat-footed like Tim Cook's Apple, you pop into scramble mode to try to catch up. Early on, you hit it with a big marketing flourish (WWDC24) in order to buy some more time. Then you dribble out features as they get finished & actually exist. Classic vaporware. https://t.co/I1J4y3aDNy pic.twitter.com/fLKvxGj4G3
— MacDailyNews (@MacDailyNews) July 31, 2024

Executing a vaporware strategy is an unfortunate necessity without a visionary CEO and it takes time to actually realize (code, test, build out datacenter infrastructure, etc.) a grand marketing vision. – MacDailyNews, September 10, 2024

You know, some people get upset when we point out that Tim Cook is a boring, reactive caretaker who’s not really the best person to be running Apple today or for at least the past several years.
Operations manager Cook should have been a 3-5 year stopgap after Steve Jobs’ untimely passing, running the iteration playbook, providing continuity for the company while it found a real CEO. Instead, he hung on — and keeps hanging on — well past his sell-by date.
Sigh.
You can be upset with us for having the temerity to call it like we see it, but the fact remains that Apple would be doing significantly better today with a visionary who’d have seen AI on the horizon, who’d have recognized the intrinsic importance of Siri and therefore invested in it instead of criminally neglecting it, and who wouldn’t have squandered the company’s gigantic leads in things like personal assistants and podcasting. – MacDailyNews, August 22, 2024

Every Apple (AAPL) shareholder should of course enjoy every new all-time high, but also never forget that with a visionary CEO instead of a myopic, iterative, virtue-signaling caretaker who’s currently on tour peddling AI vaporware* because he completely missed it by wasting… pic.twitter.com/ceecUAbJUA
— MacDailyNews (@MacDailyNews) December 6, 2024

Until it gets another visionary leader (fingers crossed; Apple’s history has shown – cough, Sculley, Spindler, cough – that the next CEO could be far, far worse than the very competent caretaker Cook), Apple can afford to miss things like generative AI – which they clearly did – and then use its huge war chest to catch up – which they’re doing right now (fun times and 80-hour weeks inside Apple Park!) – and, hopefully, [someday] surpass rivals (or at least be as good). Apple will very likely unveil their catch-up work within months (this June at WWDC 2024) in iPhones (and iPads, Apple Watches, etc.) with built-in on-device generative AI and other new AI-driven features. – MacDailyNews, February 14, 2024

Every Apple (AAPL) shareholder should of course enjoy every new all-time high, but also never forget that with a visionary CEO instead of a myopic, iterative, virtue-signaling caretaker who’s currently on tour peddling AI vaporware* because he completely missed it by wasting… pic.twitter.com/ceecUAbJUA
— MacDailyNews (@MacDailyNews) December 6, 2024

Apple needed new blood years ago, but the old blood simply won’t let go. – MacDailyNews, January 22, 2025

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