What happened in that room
The contextual, cross-app Siri Apple promised is the gap users keep pointing to. | Image by Apple
Around early 2025, Apple’s senior leadership gathered in a conference room near Craig Federighi’s software engineering group. The senior vice presidents were there, along with the COO, the CFO, design chief Alan Dye and Vision Pro lead Mike Rockwell. Tim Cook was not. Then-COO Jeff Williams, who has since retired, called the meeting to order, and the task was blunt: recommend to Cook how to fix AI.
The backdrop was ugly. Apple Intelligence had flopped, the Siri overhaul was about to slip again, and Meta, Microsoft, Google, OpenAI and Anthropic were all sprinting ahead. Cook had largely lost confidence in his AI chief, John Giannandrea, who sat right there as the group concluded Apple had a leadership problem on AI.
Federighi ran much of the discussion, but the voice that carried was Rockwell’s. Fresh off the Vision Pro launch, a technical win even if it bombed commercially, he volunteered to become Apple’s fixer for AI and Siri. Federighi and chip chief Johny Srouji recommended Cook hand him Siri, and by the Top 100 retreat in March 2025, Cook was close to signing off.
The fight nobody saw
Here is the part that never made it into the restructuring we covered earlier. Rockwell thought he was signing up to be Apple’s overall AI leader, replacing Giannandrea and reporting straight to Cook. However, Federighi pushed back hard, insisting Rockwell would run Siri but still report to him, keeping AI inside software engineering.Rockwell did not love that, as he felt Federighi had been slow to take AI seriously, and he wanted a promotion to senior vice president instead. In the end, he took Siri under Federighi anyway. Giannandrea was stripped of most of his responsibilities, and his departure from Apple followed this year. Apple later brought in former Google and Microsoft executive Amar Subramanya as a second AI leader, also reporting to Federighi.
Why this matters
This is not just water cooler gossip. The reporting lines decided here are the reason the new Siri exists in the shape it does, and the dysfunction goes back much further than 2025.
About a decade ago, former hardware chief Dan Riccio warned colleagues that AI could one day become an existential threat to Apple’s devices, and he had Rockwell draw up a five-year roadmap to overhaul Siri. Apple’s leadership was not interested at the time, and that plan died on the vine.
Over on Reddit, one user summed up the frustration with Siri’s basics. | Image by Initial_Hair_1196 via Reddit
How this stacks up against Google and Samsung
If you are on a Pixel 10 Pro or a Galaxy S26 Ultra, none of this changes your day. Gemini already does the contextual, cross-app work Apple is still trying to ship, so this is really Apple racing to close a gap its rivals closed a while ago. Should Google or Samsung be worried? Not yet, not until the rebuilt Siri actually lands and works.
I stopped using Siri a long time ago, a I just quietly accepted it was not good enough as a phone assistant. That said, I still want the new Siri to be good. However, I am just not ready to trust a turnaround that took this long and this much internal arm-wrestling to even get started.
#Insider #reveals #Apples #ugly #meeting #iPhones #Siri