Apple Cannot Be Sirious

Stop me if you've heard this before: Apple may have to delay the roll-out of some features for the new version of Siri. Oh, you have heard this before? A half-dozen times just in the past few years? Weird. It's almost like Apple is having some major issues with their AI implementation and strategy. They should probably look into that. Perhaps before Mark Gurman does for Bloomberg?

Apple Inc.’s long-planned upgrade to the Siri virtual assistant has run into snags during testing in recent weeks, potentially pushing back the release of several highly anticipated functions.

After planning to include the new capabilities in iOS 26.4 — an operating system update slated for March — Apple is now working to spread them out over future versions, according to people familiar with the matter. That would mean possibly postponing at least some features until at least iOS 26.5, due in May, and iOS 27, which comes out in September.

Fool me once, shame on you, fool me twice, shame on me, fool me a dozen times... just shame. Shame. Shame. Shame.

As I see it, Apple has two problems. The first one is the bigger one: they need to fix Siri. But the second one is tangentially related to that quest: they need to plug the leak of detailed information about the Siri roadmap and timeline.

Officially, Apple has only said that they planned to launch a new version of Siri in 2026. This is embarrassing in and of itself considering that it is functionality they promised at WWDC two years ago and infamously ran commercials about new features even though it was effectively vaporware at the time. Many of those features got pushed into 2025. And then they had to reshuffle the entire effort – including the team overseeing AI – which pushed everything into 2026. We're only two months into 2026, so normally Apple would have some time here. The problem is that they incredible amount of leaks, almost all of which result in Mark Gurman scoops for Bloomberg, have seemingly given the public far more granular details about the timing and yes, issues.

Apple is a famously secretive company, and yet these highly specific leaks have been going on for years at this point. It's honestly pretty weird. I used to do such reporting for a living with my share of Apple scoops back in the day. When those would happen, Apple would move fast and decisively to try to plug any holes, and they often would. I'm honestly not sure what to make of the fact that they haven't here – again, over years and years. And this is a perfect example of how damaging it can be to the company. Again, without these reports, no one outside the company would likely know that there are ongoing issues. Instead:

In the spring of last year, Apple delayed the rollout, saying the new Siri would instead arrive in 2026. It never announced more specific timing. Internally, though, Apple settled on the March 2026 target — tying it to iOS 26.4 — a goal that remained in place as recently as last month.

But testing uncovered fresh problems with the software, prompting the latest postponements, said the people, who asked not to be identified because the deliberations are private. Siri doesn’t always properly process queries or can take too long to handle requests, they said.

Thanks to Gurman's reporting, the entire market has been guided to expect a new version of Siri coming in that iOS 26.4 update. And given that iOS 26.3 just launched yesterday, the first beta builds of this new Siri update are undoubtedly imminent. In fact, we know the exact targeted week: February 23. How? Yet another Gurman report. On something as granular as the timing for a beta roll-out.

Anyway, everyone – including myself – was starting to get excited. Apple was finally going to fix Siri! Of course, we all had no reason to believe Apple here after 15 years of such promises, except that this time they made the hard (and correct) decision to outsource the AI work, going so far as to announce the partnership with Google to use Gemini. That's how dire the situation had become. The super secretive Apple, a company which famously aims to own and control their entire stack, had to publicly announce this partnership – with a major rival, no less – despite it being a de facto admission that they messed up Siri badly enough, and their AI strategy more broadly, that they couldn't fix it themselves.

And they had to announce this, in part, because of the reporting on the matter. Everyone knew they were weighing partnering to fix Siri. And that a bake-off was going on. And between whom. So Apple had little choice but to comment on it when it was over and Google was picked as the winner – never mind the fact that Apple may have wanted to pick Anthropic but the AI startup wanted too much money to use customize Claude, per who else... With the announcement, it looked like Apple was finally putting the AI shitshow behind them. The market cheered.

And again, thanks to these Gurman reports, we knew to expect to see some progress shortly with these beta builds. Not so fast...

In recent days, Apple instructed engineers to use the upcoming iOS 26.5 in order to test new Siri features, implying that the functionality may have been moved back by at least one release. Internal versions of that update now include a notice describing the addition of some Siri enhancements.

One feature is especially likely to slip: the expanded ability for Siri to tap into personal data. That technology would let users ask the assistant to, say, search old text messages to locate a podcast shared by a friend and immediately play it.

The tapping into personal data feature was literally the marquee selling-point of Siri in that WWDC 2024 keynote. We're clearly going to go a full two years without Apple being able to ship that, even despite the Google partnership.

To be clear, I found it a little odd that the timing of the first Siri fixes were coming so soon after Apple announced the partnership. While there are undoubtedly some things that the two sides could plug-and-play, it seems like there might be a million little edge cases for things that would break when swapping models. And well, they're breaking...

Testers have also reported accuracy issues, as well as a bug that causes Siri to cut users off when they’re speaking too quickly. And there are problems handling complex queries that require longer processing times.

Another challenge: The new Siri sometimes falls back on its existing integration with OpenAI’s ChatGPT instead of using Apple’s own technology. That can happen even when Siri should be capable of handling the request.

Again, these details are beyond embarrassing. And makes it seem ridiculous that Apple would tout the partnership publicly – certainly without giving an updated time frame as to when to expect the fruits of such labor. Instead, we have all been going off of Gurman's reporting. And so when timetables inevitably slip...

It's more egg on the face for Apple!

And while you might think the public doesn't care about such things, the "Siri sucks" narrative has clearly gone mainstream. As has the "Apple is behind in AI" talk, which had been problematic for their stock price. Yes, it has bounced back a bit thanks in part to being a hedge against the Big Tech CapEx situation, but more so on the resurgence of the iPhone sales. But still, Apple spent years and years as the most valuable company in the world, now they're battling to stay in second or even third place on most days. Why? AI of course. Whether or not you believe in its value right now, the long-term prospects have boosted all of their competitors. And it has fueled this narrative that Apple is behind, and continuing to slide.

You know what doesn't help that narrative? Reports that Siri continues to slip...

Anyway, my point is that it's wild how Apple cannot plug these leaks when its so clearly hurting the company in very tangible ways. But yes, the bigger issues seems to remain that they cannot fix Siri.

And while I was excited for this Google partnership and for Apple to put this sad chapter behind them, I'm no longer sure they'll actually be able to. And that Siri may continue to suck for the 15th year in a row...