I want to love the new Siri in iOS 27. Apple calls it Siri AI, and it’s supposed to be smarter, more powerful, and faster. Sometimes, I’m impressed by the things it can do.
When I linked to David Pogue’s piece about all the ways he was using Siri AI, I was excited by that list. David wrote about the powerful things he got Siri to do, and about the hardest part of using the new Siri: remembering to use it after years of being underwhelmed by how Siri operates.
I am remembering to use it more. But it’s also pissing me off a lot again.
There’s one new feature of Siri that seems like a positive in theory, but in practice I find rather infuriating: When Siri isn’t quite sure it heard you properly, it seeks clarification.

Here’s one example. I needed to remember to send Donna photos of my kitchen. I asked Siri to remind me to send Donna photos on a specific day, at a specific time. Siri wasn’t sure what name I’d said, so it asked which of four names I’d been trying to say. Then I had to speak to Siri again to clarify. Then it set the reminder.
I get this kind of interaction all the time. Something about my diction doesn’t work for Siri, I guess.
The first problem is that sometimes providing the requested clarification is extremely annoying. The second problem is that it slows the whole process down.
I would much prefer that Siri set the reminder to send Donna photos—using the first name it thought I’d said, which was exactly correct—and then say: “I set a reminder to send Donna photos. If you said one of these other three names, let me know.”
Then I could move on with my day. Siri could make the most likely guess, and I could correct it if necessary.
I have another annoyance with the new Siri when I’m setting appointments, which used to work just fine under the old Siri. I have all kinds of annoying interactions when it comes to setting appointments, but here’s one from just this morning.

I was setting an appointment to go to the gym tomorrow. After I provided the event’s date and time, Siri asked me to provide both again. Then, before I could respond, it set the appointment anyway.
Except it assumed I meant I wanted to go to a human being named Jim, as opposed to the workout place. Contextually, I think that’s a bad guess.
It also appears that Apple is rolling out iOS 27 more slowly than in previous years. David Smith’s adoption data from Widgetsmith and Pedometer++ shows a slower rollout, which he suspects is deliberate, to help manage the Siri AI waiting list.
John Gruber wrote about this yesterday at Daring Fireball, and he thinks that explanation makes sense, too. In that same piece, Gruber wrote that Siri AI feels slower and sometimes gives worse answers than it did over the summer. He was careful to describe that as his personal experience, rather than a definitive finding. But it matches my experience, too.
All of this is to say: I’m trying to train myself to use Siri more. And I am more impressed by some of the powerful things it can do.
But in general, I’m just as annoyed by it as I’ve been for years when it makes common, frustrating mistakes that the other assistants and AI tools in my life don’t struggle with nearly as much.