The big Siri Apple Intelligence delay proves that maybe we really don’t know Apple at all

• March 14, 2025

Most quotes about disappointment focus on the bright side: “Disappointment is a detour on the road to success,” said Zig Ziglar. Maybe he’s right but when the disappointment leads to an immutable fact or harsh realization, there may be no coming back from it. The Siri Intelligence delay and subsequent fallout is that kind of disappointment and became a wake-up call of sorts as everyone is reassessing their Apple point of view.

I’m sure by now many of you have read the various analyses and excoriations of Apple’s failure to deliver on its Apple Intelligence and Siri promises. My favorite, by far, is Daring Fireball’s epic “Something Is Rotten in the State of Cupertino” exploration of what went wrong and how “Apple pitched a story that wasn’t true.”

Our own John-Anthony Disotto calls Apple Intelligence “a fever dream” that perhaps Apple might like to forget. Fast Company’s Harry McKracken is a bit more measured and while he thinks Apple might’ve failed to “emotionally bond with Siri” he writes that he’d rather see a “great” Siri than one that arrives “on time.”

In some ways, they’re all right. Apple is the most credible tech company on the planet. It did over-promise and create this mess, and sure, I’d like to see the very best Siri possible and, honestly have no choice but to wait for it.

But my disappointment is rooted in something far deeper and more disturbing than just Siri.

The long wait for a smarter Siri

I’ve been chatting with Siri for almost 15 years and, in the early days, was impressed with its almost conversational capabilities. I wrote in detail about its numerous brain transplants and speech updates. Even as Alexa overtook it, I knew we were still in the horse-and-buggy stage of AI and I waited patiently for the magic I knew only Apple could bring.

My patience began to wane during the early days of the AI revolution as OpenAI and ChatGPT took the world by storm and then Microsoft supercharged awareness with Bing AI and eventually Copilot. Apple seemed to be sitting on its hands as Google and Samsung showed off impressive native AI feats in apps, on the web, and in Galaxy and Pixel phones, respectively.

WWDC 2024 changed all that and gave me hope that Apple was in the AI race, but there were worrisome signs even back then that because, well, it was Apple, I chose to ignore or forgive.

Chief among them was that Apple was quickly ceding key AI elements to the competition. The integration of ChatGPT and Google for complex natural language prompts was seen as a win, but it was also Apple throwing up its hands and saying, “Here. You handle this.”

Anything more complex than “Hey Siri, play my Pump Up playlist” is handed over to ChatGPT. Essentially you are leaving Apple land for a world managed by an open source AI platform, albeit arguably the best one in the world.

I cut Apple slack because of the big promise: Siri would get better and not by a little bit. It would be the intelligent assistant you dreamed of. An AI that, with your permission, could see all on your best iPhone and on its screen. It could take action based on your written or spoken prompts, and keep the conversation going so you got the best result out of Apple’s ecosystem and all your data that’s embedded in it.

I believed because, like so many others, we believe in Apple.

When they were magical

Apple is a special company. It all but appropriated the word “magical.” Nobody launched products like Apple. No company has the aura. Its chief executives are mythical creatures. CEO Tim Cook is a bona fide celebrity and his warm Alabama cadence can lull you into submission: yes, Apple will do that.

But the hard realization is that Apple is just another tech company and one that is facing perhaps its most difficult technical challenge.

Yes, I appreciate the transparency. I’ve worked on many projects that took longer than I anticipated. It’s hard to tell your boss: this will be delayed. For Apple, it had to share the news with almost a billion users.

Over the years, I’ve seen Apple fail or underdeliver and watched how it’s held to an almost higher standard than others. Its efforts to bring us the thinnest phone ever resulted in the possibly bendable iPhone 6 but Apple recovered with a stronger iPhone 7 and future designs that almost challenged you to bend them.

Apple’s not great at apologies. 15 years ago, the late Steve Jobs held an apology, non-apology press conference to explain away “Antennagate.” For those who don’t recall, that was when the iPhone 4 came out and some people reported connectivity issues that may have been related to their hands covering the ill-positioned antennas on the outside of the phone. The company initially said we were holding the phones wrong, and then Jobs held that press conference to clear the air. Sort of. He never exactly apologized and did his best to minimize the issue and encourage reporters to move on.

It’s not that Apple is incapable of admitting fault.

The art of the apology

Back in 2017, Apple invited me to Cupertino to talk about a Mac Pro do-over. This was unheard of. Not only was Apple saying it made a mistake, it was detailing where it went wrong and how it planned to recover and deliver a new Mac Pro for its devoted creative and development customers.

Oddly, what I did not take away from that day is that Apple is fundamentally a company like any other, with hits and misfires, and delays and struggles.

Similarly, I did not take Apple Intelligence promises with a grain of salt. Even as the company slowly stepped its way through delivering fresh AI updates, I waited patiently – and confidently for the big Siri update. I did have some frustration and tried, in my own way, to cajole Apple into action.

Even though Apple operates in secret, rumors and leaks are surprisingly precise about future activities. And for the longest time, they had the big Siri reveal pegged to iOS 18.4. When that didn’t come, I was confused. And when Apple admitted that the update would be delayed to “in the coming year” I was surprised and upset.

That’s when it finally sunk in.

My understanding of Apple as this precise and near perfect and well-oiled machine was, if not wrong, artificial. Yes, it is a massive and highly accomplished company with a spectacular campus that has done more to change the world than most, but it’s also a gigantic enterprise of regular people operating in a demanding corporate bureaucracy trying to solve difficult engineering and programming challenges. Some of that is in evidence if you go by the latest Apple leak from Bloomberg, which describes an internal Apple meeting that sounds very much like your typical frustrated tech company leadership.

I don’t know what went wrong, if it was the scale of the problem, the lateness of Apple’s AI start, or someone inside over-promising about what they could deliver and when, but I should not have been so surprised.

Apple’s not special. It’s just a great company that often delivers great things. And sometimes it doesn’t and we have to accept that.

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Most quotes about disappointment focus on the bright side: “Disappointment is a detour on the road to success,” said Zig Ziglar. Maybe he’s right but when the disappointment leads to an immutable fact or harsh realization, there may be no coming back from it. The Siri Intelligence delay and subsequent…