The battle to rework the failed Apple Intelligence initiative and Siri stems from a fateful meeting of executives, that triggered a major restructuring of Apple’s AI efforts. Here’s what happened, and when it all went down.

Monday’s WWDC keynote address is expected to be heavy on AI features in iOS 27 and Apple’s other operating systems.

It should also bring to an end a turbulent period for the company. After the initial launch of Apple Intelligence and its seeming failure, as well as repeated delays for the promised Siri revamp, it had to do something.

Over the last two years, Apple had to make changes, which also included a considerable restructuring of its AI work. According to Mark Gurman in Sunday’s “Power On” newsletter for Bloomberg on Sunday, the overhaul effort stemmed from a meeting in early 2025.

A big AI meeting

At the time of the meeting, Apple was facing an industry that was moving extremely fast, leaving its own AI work behind. Executives met in a conference room near the software engineering department to try and solve the problem.

Though CEO Tim Cook wasn’t there, now-retired COO Jeff Williams was the one who called the meeting to order. Other executives in attendance include multiple C-level executives, as well as former interface design chief Alan Dye and Apple Vision Pro lead Mike Rockwell.

The meeting was all about the crisis that was Apple Intelligence and the looming prospect of a delayed Siri update. Executives quickly realized the scale of the problem, and its impact on Apple if changes didn’t happen soon.

Siri on an iPhone.

The meeting then moved to make a recommendation to Cook about Apple’s response. At the time, Cook had little confidence in then-AI chief John Giannandrea, also in attendance at the meeting.

Software chief Craig Federighi led most of the talks, but Rockwell volunteered to take the role to fix AI and Siri. Rockwell’s credibility was high, following the launch of the Vision Pro headset, which helped his cause.

A decade previously, former hardware head Dan Riccio raised the need for an AI leader to be on the Apple executive team. He also told Rockwell to make a five-year plan to rework Siri.

However, at the time, the top executives weren’t that receptive to the idea, and the Siri roadmap wasn’t completed. By the 2025 meeting, the same group of executives believed that there needed to be some leadership changes, and recommended to Cook for Rockwell to manage Siri.

Siri, not all AI

While Rockwell was recommended and Cook was close to approving the plan in March 2025, it wasn’t a done deal.

At the time, Rockwell thought he was working to become Apple’s AI leader in general, replacing Giannandrea. Federighi, however, believed that Rockwell should oversee Siri and report to him, instead of directly to Cook.

Rockwell considered that Federighi wasn’t seeing AI as being important, and then started to back away from the Siri role. With a yearning to become a senior vice president, Rockwell wanted promotion, but eventually agreed to the Siri position under Federighi.

Model behavior

That Siri role decision meant that Apple still had to find someone to deal with AI models, which led to a a long period of headhunting in 2025. Eventually, Amar Subramanya was picked to be the second AI leader, again reporting to Federighi.

Google Gemini is being used to help create Apple’s models.

However, Apple still had to catch up with the rest of the industry. To that end, Rockwell started to look at ways to do so, including using third-party solutions.

That eventually resulted in Rockwell, Federighi, and Eddy Cue making a deal with Google to use Gemini and Google Cloud to jumpstart creating the new Apple Foundation Models.

More Cook than usual

While the meeting was a big driver for AI, Apple’s seeming failure at the time also led to more input from Cook. At the time of the meeting, Cook decided to inject himself into work on the AI roadmap, making more decisions about plans, and even delivered an AI pep talk to the company.

Cook became a lot more hands-on with AI than he normally would for company projects. Roadmap and key decisions were previously left to his reports, with Cook usually taking a light-touch approach to management, but not for AI.

He urged Federighi and others to treat AI more seriously and to make it a success.

Federighi, in charge of implementing AI features, has adjusted his view and handling of the technology. He now views it as the central focus of operating system upgrades for years.

That early 2025 meeting was a turning point for Apple’s AI work, and came at a crucial time for the company. We won’t know if it has done enough until the Keynote video begins on Monday.