Apple’s AI struggles reportedly sparked a major internal reckoning in early 2025, when senior executives gathered for a private meeting to address growing concerns about the company’s position in artificial intelligence.
According to Bloomberg’s Mark Gurman, the discussion focused on the disappointing rollout of Apple Intelligence, delays to Siri’s next-generation upgrade, and the rapid progress made by rivals including OpenAI, Google, Microsoft, Meta, and Anthropic.
The meeting reportedly became a turning point for Apple’s AI strategy. Executives concluded that the company needed major leadership and structural changes if it wanted to remain competitive in the fast-moving AI race.
That process eventually led to Vision Pro creator Mike Rockwell taking charge of Siri, while software chief Craig Federighi assumed a much larger role in shaping Apple’s AI future.
“Apple’s AI crisis ultimately wasn’t only about Siri the product. It was about a company that had spent decades setting the direction of the technology industry suddenly finding itself behind. The decisions made during that pivotal executive meeting were acknowledgements that the old approach was no longer working.” — Mark Gurman, Bloomberg
Those decisions are expected to take center stage at WWDC 2026, where Apple is preparing to unveil a revamped Siri alongside iOS 27, macOS 27, watchOS 27, and other software updates. Gurman reports that Apple will introduce a more conversational Siri experience and a dedicated assistant app designed to compete more directly with modern AI chatbots.
The upcoming announcements carry added significance because they represent Apple’s first major attempt to prove that it can catch up in artificial intelligence after a difficult start. With Tim Cook entering the final phase of his tenure as CEO, WWDC 2026 will offer the clearest look yet at whether Apple’s internal AI reset is beginning to pay off.
