Apple’s AI-powered Siri overhaul has been delayed to 2026-2027 – the third postponement for a feature the company was running ads for in 2025. The AI chief is retiring. Investors have “gotten enough gray hairs waiting.” The world’s most valuable company is learning what Google learned in 2022: being an incumbent during a paradigm shift is the hardest position of all.
The timeline tells the story. The new Siri – a more personal, context-aware assistant capable of complex tasks and deep app integration – was originally planned for 2025. In March 2025, Apple delayed it after running ads for features that didn’t work. Now it’s pushed to 2026 at the earliest, with some reports suggesting 2027.
Apple engineers have been racing to fix bugs unsuccessfully. Internal concerns suggest fixing Siri requires more powerful AI models running on devices, which could strain hardware. In early December, John Giannandrea, Apple’s machine learning and AI strategy chief, announced retirement for 2026. The consensus: 2026 is “make-or-break” for Apple’s AI credibility.
Framework Analysis
Apple faces the classic incumbent’s paradox. The company that perfected the smartphone cannot easily pivot to AI-first interfaces without disrupting its core product. Every AI feature that works too well makes Siri the interface instead of iOS – cannibalizing the ecosystem Apple spent 17 years building.
Apple’s lack of AI spending has concerned investors – the company hasn’t matched hyperscaler infrastructure investments. While Microsoft spends $80 billion and Google acquires Intersect for $4.75 billion, Apple’s AI strategy remains unclear. The smart glasses expected in 2026-2027 may arrive to a market where Meta has 60% share and years of iteration advantage.
Apple’s delays mirror every incumbent facing paradigm shifts. The capabilities exist but deployment threatens existing revenue. The organization optimized for the old paradigm resists the new one. Without a Code Red moment forcing transformation, the delays compound.
Key Takeaway
Apple’s Siri delays to 2027 and AI chief retirement signal the incumbent’s hardest challenge: transforming when the existing business still generates hundreds of billions. 2026 is make-or-break.
Gennaro is the creator of FourWeekMBA, which reached about four million business people, comprising C-level executives, investors, analysts, product managers, and aspiring digital entrepreneurs in 2022 alone | He is also Director of Sales for a high-tech scaleup in the AI Industry | In 2012, Gennaro earned an International MBA with emphasis on Corporate Finance and Business Strategy.
