In early 2025, a group of Apple’s top executives gathered in a conference room — without Tim Cook — and confronted a harsh reality: the company was dangerously behind in the AI race. That closed-door meeting sparked a dramatic turnaround, reshuffling leadership on Siri, pulling Cook deeper into the fray, and setting the stage for one of the most significant software overhauls in Apple’s history.
As WWDC 2026 kicks off, the results of that pivotal moment arrive with iOS 27, a revamped Siri that’s finally embracing modern AI capabilities, user-selectable models, and deeper on-device intelligence.
Mark Gurman for Bloomberg News:
The assembled leaders included the company’s senior vice presidents, chief operating officer, chief financial officer and others who reported to Chief Executive Officer Tim Cook. Alan Dye, Apple’s former interface design chief, and Mike Rockwell, the creator of the Vision Pro headset, were also present.
The discussion centered on what had by then become a growing crisis: Apple Intelligence, the company’s new AI platform, was a flop, and a critical overhaul of the Siri digital assistant was on the verge of being delayed.
At the same time, rivals such as Meta Platforms Inc., Microsoft Corp., Alphabet Inc.’s Google, OpenAI and Anthropic PBC were rapidly advancing. During the meeting, executives discussed just how much trouble the company was in if real changes weren’t made immediately…
The purpose of the meeting quickly became to formulate a recommendation to Cook about how the company should respond. By that point, Cook had largely lost confidence in then-AI chief John Giannandrea, who was also in the room. Cook and several executives close to him had concluded that Apple had serious cultural, structural and leadership problems when it came to AI.
Giannandrea was stripped of much of his portfolio and left this year. With Rockwell focused on Siri, Apple still needed someone to oversee AI models and research. For much of 2025, company headhunters scoured rivals for a second AI leader to report to Federighi, ultimately landing on former Google and Microsoft engineering executive Amar Subramanya.
This Monday, the result of those decisions will take center stage when the company introduces a revamped Siri at its Worldwide Developers Conference. By many accounts, Rockwell taking the job — and Federighi getting religion on AI — was a pivotal moment in Apple’s history… As for Cook, Apple Intelligence 1.0 and the first attempt at launching the new Siri represent a black mark on his resume. He recently told employees that Apple Maps was one of the biggest failures under his watch, but that debacle pales in comparison to Apple’s AI efforts — at least so far.
MacDailyNews Take: Tim Cook’s years-long mishandling of Siri and his total miss on the AI revolution are the primary reasons he is Apple’s outgoing CEO today.
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The post The wake-up call: How a secret 2025 meeting forced Apple to finally begin trying to catch up in AI appeared first on MacDailyNews.
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