The failed Apple Intelligence initiative and the battle to rework Siri stemmed from a fateful meeting of executives that prompted a major overhaul of Apple’s AI efforts. Here’s what happened when it all went down.
Monday’s WWDC keynote is expected to be heavy on AI features in iOS 27 and Apple’s other operating systems.
This should end a turbulent period for the company. After the initial launch of Apple Intelligence and its apparent failure, as well as repeated delays to the promised Siri overhaul, it had to do something.
Over the past two years, Apple has had to make changes, including a substantial overhaul of its AI work. According to Mark Gurman in Sunday’s “Power On” newsletter Bloomberg On Sunday, the restoration effort evolved from a meeting in early 2025.
A great AI encounter
During the meeting, Apple faced an industry that was moving too fast to abandon its own AI work. Executives gathered in a conference room near the software engineering department to try to solve the problem.
Although CEO Tim Cook wasn’t there, now-retired COO Jeff Williams called the meeting to order. Other executives in attendance included several C-level executives, former interface design chief Alan Dye and Apple Vision Pro lead Mike Rockwell.
The meeting was about Apple’s intelligence crisis and the prospects for a delayed Siri update. Executives quickly realized the scale of the problem and the impact on Apple if changes didn’t happen soon.
Siri on iPhone.
The crowd moved to recommend Apple’s response to Cook. At the time, Cook had little faith in then-AI chief John Gianandrea, who attended the meeting.
Software chief Craig Federighi led most of the talk, but Rockwell pitched in to fix AI and Siri. Rockwell’s credibility rose following the introduction of the Vision Pro headset, which helped his cause.
A decade ago, former hardware chief Dan Riccio raised the need for an AI chief on Apple’s executive board. He told Rockwell to create a five-year plan to rework Siri.
However, at the time, top executives were not receptive to the idea, and the Siri roadmap was not completed. At the 2025 meeting, the same board of executives believed that some leadership changes were needed and recommended Cook for Rockwell to manage Siri.
Siri, not all AI
Although Rockwell was recommended and Cook was in a position to approve the plan in March 2025, it was not a deal.
At the time, Rockwell was thought to be working to replace Gianandria and become Apple’s head of AI in general. Federighi, however, believed that Rockwell would oversee Siri and report to Cook instead of reporting directly to him.
Rockwell felt that Federici didn’t see AI as important, and then began to back away from the Siri role. Longing to become a senior vice president, Rockwell wanted a promotion, but eventually settled for a Siri position under Federici.
Model behavior
That Siri stock decision means Apple still needs to find someone to handle the AI models, leading to long-term interventions in 2025. Eventually, Amar Subramanya was chosen as the second AI chief, again reporting to Federighi.
Google Gemini is used to build Apple models.
However, Apple still had to catch up with other parts of the industry. To that end, Rockwell began looking at ways to do so, including using third-party solutions.
As a result, Rockwell, Federici, and Eddie Cue signed a contract with Google to use Gemini and Google Cloud to develop new Apple Foundation models.
Cook longer than usual
While this meeting was a big driver for AI, Apple’s apparent failure at the time also led to more input from Cook. During the meeting, Cook decided to put himself to work on the AI map, making further decisions about projects and also giving an AI pep talk to the company.
Cook has been much more used to AI than is typically applied to enterprise projects. While the roadmap and key decisions were previously left to his reports, Cook took a light-touch approach to management in general, but not to AI.
He urged Federici and others to take AI more seriously and make it a success.
Federighi, who is in charge of implementing AI features, has adjusted his vision and handling of the technology. He now considers it a central focus of operating system optimization for years to come.
The meeting in early 2025 was a turning point for Apple’s AI work, and it came at a critical time for the company. We won’t know if it did enough until the main video debuts on Monday.
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