Execs to work on a roadmap during upcoming retreat

Siri’s upgrade to leverage Apple Intelligence will be a focus at Apple’s annual retreat.

Apple’s ongoing promise to improve its vocal assistant Siri with Apple Intelligence has still not been fulfilled, and looks to be a failure at multiple levels of the executive management team.

The head of Apple’s Siri efforts, Robby Walker, has at least privately acknowledged the problems, calling them “embarrassing” and “disappointing.” Apple’s advance marketing of features that weren’t yet ready has been, he acknowledged, part of the problem.

It’s clear, based on the marketing of the features that began late last year, that Apple — or at least its marketing department — expected more Apple Intelligence features to have arrived by now, reports Bloomberg. This would have included Siri gaining on-screen awareness, personal context, and improved voice control — both of which are now officially delayed.

It’s now expected that these features may not fully roll out until sometime in 2026. It’s an unusual miss from a company that generally delivers on features when it says it will.

Pushing forward rather than rethinking

To be clear, Apple is allowed to have unexpected problems. No Apple product is perfect, but broadly speaking the company delivers software, services, and hardware that often delight users, an suffers fewer “deadline misses” than its competitors.

In most companies, a delay like this would be accompanied by the company saving face by announcing the resignation of an executive in charge of the delayed rollout. Apple’s executive team, however, are apparently a tight-knit group that has to tolerate occasional misfires like this rather than dare to lose someone — or bring in anyone new.

Big transitions at the top of Apple’s team are rare: Tim Cook has been CEO since 2011, Jeff Williams has been the company’s COO since 2010. Most of the various hardware and software division heads have been in those positions since at least 2012.

Collage of eight Apple senior executives and CEO, each with names and titles below, on a light background.
Some of Apple’s current top executives.

This week, 100 top Apple executives will be meeting for their annual retreat — and the top topic for discussion is likely to be how to speed up the evolution of Apple Intelligence, particularly to improve Siri’s interactions with users.

Traditionally, Apple has been tight-lipped about new features and abilities until the company was sure it was ready to ship — but that didn’t happen in this case. Apple Intelligence brought the promise of a “smarter” Siri, compared to the incremental and minor updates since its initial release.

That said, users would benefit immensely from the “personal context” understanding of users Siri will gain from Apple Intelligence. The reason this hasn’t already happened is that Apple Intelligence doesn’t yet include that feature, except in beta.

The folly of pre-announcements

Publicly, the delays with Siri and Apple Intelligence look like Apple’s top brass are unwilling to take any blame for failures or missed deadlines. A seemingly-permanent executive is reassuring when the company is firing on all cylinders — but recent missteps like these suggest that some rethinking and fresh voices should be considered at this year’s retreat, and going forward.

Despite the delays to key parts of Apple Intelligence and Siri, we can expect the same group of top Apple executives to make the trek to luxury resort Carmel Valley Ranch, as they have for the past several years. This year, it could be an opportunity for Apple’s leadership to refocus on getting announced services and productions out the door — and to not announce things before they’re ready.

The annual retreat could be an opportunity for all the various executives to come together and work out a detailed plan to deliver the rest of Apple Intelligence’s promised features to users quickly. While the general public may not have much awareness of the coming upgrades, Apple’s most dedicated fans are growing impatient for long-promised upgrades.

Apple has since pulled TV advertisements touting Apple Intelligence until the most anticipated features are ready to roll out. But Apple’s timeline has slipped, and a much-improved Siri is now not expected to debut until the arrival of iOS 19, which is expected to launch in the autumn of 2025.

Importantly, iOS 19 and macOS 16 will — at a minimum — need to be ready in time for beta-testing the new features and integration with developers in time for June’s annual WWDC conference. The biggest change in Siri’s capabilities since its introduction in 2011 will need to have a smooth roll-out for Apple to even begin to catch up with its rivals, including Google’s Gemini and Microsoft’s Copilot AI engines.

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