Apple Intelligence was supposed to finally deliver a more natural version of Siri, but now, people who work in Apple’s AI department believe the company won’t release a ”true modernized, conversational version of Siri … until iOS 20 at best in 2027,“ writes Bloomberg’s Mark Gurman in today’s Power On newsletter.

Apple is expected to roll out an LLM-powered Siri upgrade in iOS 18.5, but Gurman says this will work as its own separate model from the old Siri, a system that “doesn’t work as smoothly as it could.” According to Gurman, the modernized Siri would merge the two into a new architecture that can handle both simple requests, like setting timers, and the advanced AI-powered abilities Apple showed off last year, like carrying out tasks across apps using context like personal details and what’s on your screen. Apple planned to introduce this combined Siri architecture in iOS 19.4, but it’s “running behind” and “won’t be unveiled in June,” when the company usually holds WWDC, Gurman writes.

Amazon reportedly struggled with its own AI assistant upgrade of Alexa; Amazon head of Devices and Services Panos Panay told my colleague Jennifer Tuohy that the new Alexa Plus system has involved a “hundred percent re-architected” system that blends the old Alexa with the new. That’s now coming in early access soon, though only to certain devices.

Apple is on the same path but with extra challenges. Gurman reports that people in Apple’s AI department say its models “are reaching their limits,” but the company has had a hard time securing the AI training hardware it needs to improve things. At the same time, he writes that the department has been plagued by “ineffective leadership” and workers defecting to rivals, all while those rivals seem to be pushing farther and farther ahead.