Apple is set to show off a major Siri overhaul at this year’s WWDC, and the turnaround traces back to a single meeting where the company finally admitted its AI was in trouble, according to Bloomberg’s Mark Gurman.
The wake-up call came in early 2025, when a group of Apple’s top executives, including the senior vice presidents, the COO, and the CFO, gathered near Craig Federighi’s software engineering department. Tim Cook wasn’t there. The hard truth on the table was that a big Siri overhaul was about to slip again while OpenAI, Google, and Microsoft were racing ahead. A few weeks later, Eddy Cue said out loud what the room was worried about, warning that AI could upend the iPhone business within a decade.
By then Cook had mostly lost faith in his AI chief, John Giannandrea, who was in the room. Cook and his inner circle decided Apple had real culture, structure, and leadership problems when it came to building AI.
One name kept coming up: Mike Rockwell, the guy behind the Vision Pro headset. Rockwell had been pushing Apple to take AI seriously for a while, backed up by old warnings from former hardware chief Dan Riccio, who thought AI could one day become a threat to Apple’s whole product lineup. At the meeting, Federighi and Johny Srouji, now the chief hardware officer, told Cook to hand Siri to Rockwell.
There was a quick power struggle before the Top 100 retreat in March 2025. Rockwell wanted to push out Giannandrea entirely and report straight to Cook. Federighi pushed back and said software engineering should keep Siri and AI, so Rockwell would report to him instead. That’s how it reportedly played out, according to Gurman’s sources. Rockwell took over Siri under Federighi, Giannandrea lost most of his role and later left, and Apple brought in former Google and Microsoft exec Amar Subramanya to run AI models and research.
Once Rockwell was in, he swapped out Siri’s old leadership for the people who built the Vision Pro and visionOS. He, Federighi, and Cue also cut a deal with Google to swap the models and cloud behind Siri for Gemini and Google Cloud.
Cook usually is pretty hands-off on product, but this time he got deep into the AI road map, calling shots on features and direction. He told his team to move faster, convinced they’d been behind from the start. Generative AI just wasn’t on Apple’s radar when ChatGPT launched in 2022.
WWDC, which kicks off tomorrow, is where all of this finally shows up. Expect a chatbot-style Siri and a standalone assistant app meant to go up against ChatGPT. Stay tuned for the full unveil, folks.
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