Hey Siri, What’s Wrong With Apple?

She has no idea

Image by ChatGPT via prompts from the author

I’ve been a fan and advocate of Apple’s products and services since I got my first Mac (a Mac Plus) in 1986. The company has always “gone its own way,” primarily due to its visionary co-founder Steve Jobs. That word “visionary” is justified: Apple’s decades of innovation in a constantly changing field stem from one man’s singular vision for not only how people use technology, but also how technology itself can shape our lives in ways no one could have imagined. This is exemplified in one of Jobs’ famous quotes:

“Some people say, ‘Give the customers what they want.’ But that's not my approach. Our job is to figure out what they're going to want before they do … people don't know what they want until you show it to them.”

Needless to say, we’re a long way from those halcyon days of “just one more thing.” In 2011, sensing that his time on Earth was running out, Jobs chose Tim Cook to succeed him. Jobs cited Cook’s expertise in operational skills and supply-chain management, both of which were crucial to Apple’s continued growth. Jobs also knew that Cook was willing to work outside his comfort zone and, most importantly, admit when he made a mistake.

It was a good choice at the time, and Cook has guided the company with a steady hand for many years. However, he was never a visionary — very few people are — and over the last couple of years, he has repeatedly stumbled without acknowledging his mistakes. Worse, he’s actively denied that anything is wrong. What led to these events, which could result in Cook stepping down next year? You guessed it: A.I.

It’s “under promise, over deliver,” not the other way around

The flashpoint for one of the most embarrassing missteps in Apple's history was 2024’s Worldwide Developers Conference (“WWDC”), held each June. It’s a week-long event where the people who write software for Apple devices gather at Apple Park in Cupertino to attend workshops, demos, one-on-one sessions and more. And it always starts with a keynote address that centers on software — mainly the next operating systems for all Apple devices — along with occasional hardware announcements.

By 2024, AI was everywhere, and people were wondering when Apple would make a splash. OpenAI’s ChatGPT was already a household word, and it was apparent that the “AI Arms Race” had begun. Apple’s classic approach to new tech they didn’t originate has always been to let everyone take their best shot, then swoop in with a version that’s better, faster, prettier and easier to use. (Notice I didn’t say “cheaper.”) Most pundits, including me, believed that Apple’s entry into AI would dominate the 2024 WWDC keynote… and we were right.

Tim Cook unveiled “Apple Intelligence” that day, showing the world what anyone who’s ever used Siri has wanted since Siri debuted: a Siri that understood “context.” In a mind-blowing demo, Apple execs showed how Siri could now understand what you were saying, not only understand, but also grasp the meaning behind what you said. For example, asking Siri, “When should I pick up my mom from the airport?” Usually, Siri would ask for more information or give up. This time, by parsing your emails, calendar items, texts and more, Siri could figure out what you were asking because it would know who “mom” is, what flight she was on, what airport she was arriving at, and even the traffic patterns. People were floored.

Many other features of Apple Intelligence were introduced that day, but what I called “Super Siri” is all anyone wanted to talk about. In coy Apple fashion, there was a mention that the new enhanced Siri was coming “sometime later this year.” Along with the Apple Intelligence announcements, there was also a push to sell the latest iPhone 16 models coming that fall, as they were advertised as “built for Apple Intelligence.” The implication was clear: if you want the magic, you’ve got to upgrade your hardware to make the magic happen.

What we didn’t know at the time was that those Super Siri demos were all “canned” — that Super Siri was a myth.

Lighting the fuse

While the core features of Apple Intelligence — including email and text summaries, Safari search result summarization, writing tools in Mail and elsewhere, Image Playground, and GenMoji, as well as CleanUp in the Photos app — are handy, they are not setting the world on fire. While it’s convenient to have these features built into the core software you rely on, other companies, such as ChatGPT and Grammarly, have already been there for a while with seamless integration and useful features. (I regularly use both.)

After Super Siri failed to materialize in 2024, the company went silent on the issue. There had been a few articles by then that examined the situation while wondering what was going on. The essay that set off seismic waves around the world was veteran tech journalist John Gruber’s searing March 12, 2025, bombshell post, “Something Is Rotten In The State Of Cupertino.”

Gruber’s “Daring Fireball” website has been a reliable mainstay of Apple news, opinion and insight for as long as many of us can remember. He, like I, has also been a longtime fan and user, so to write something like this — as painful as it was — took a real act of courage. And it got the world’s attention, especially the claim that Super Siri was “vaporware” — that it never really existed. And Apple doesn’t do vaporware. The article hit a nerve.

Within weeks, there were entire division shakeups at Apple. Department heads were out, divisions were reorganized, and priorities shifted. Within a few more weeks, stockholders filed a class-action lawsuit regarding said vaporware, with another filed by a group with a credible claim that Apple had misled people into buying new iPhones based on a false promise. Behind closed doors, many Apple execs were also embarrassed at these very public missteps.

And now that the 2025 WWDC has come and gone with no mention of Siri at all and the news that an “enhanced” Siri won’t happen until Spring 2026, a third class action lawsuit was filed just four days ago for allegedly “downplaying how long Apple needed to integrate advanced artificial intelligence into its Siri voice assistant.”

It’s easy to assume these delays were caused by the task being harder than anyone imagined. However, the Mac Stories team has another angle that has merit: the issue of security. Their article, which came out a few days before John Gruber’s, takes into account Apple’s unwavering stance on personal security and how easily Siri and other Apple Intelligence tools could be used to compromise that security. If AI knows everything about you, how easy would it be to trick it into revealing that info to others? This is something that other companies need to explore, but as far as I can tell, it’s taking a back seat to whiz-bang features. We all need to slow down a bit.

It’s Time For Apple To Get Its Mojo Back

2025’s recently completed WWDC had some significant announcements that further extend Apple Intelligence’s reach (assuming these are real features and not smoke and mirrors), such as Live Translation: the ability to converse with someone who speaks another language in real-time. Additionally, the new Liquid Glass look that all operating systems will receive this fall is not only visually appealing but also functional. For the first time, all Apple devices will have the same “look and feel” (plus the same version numbers!) for a consistent user experience. Great!

But… but… why doesn’t the Photos app have AI-based face enhancement yet? There are at least a dozen websites like Remini AI that offer this; some are even free (although with limited functionality). Apps like Photoshop now also have a similar function. Earlier this year, Apple bought the esteemed photo manipulation app “Pixelmator,” so maybe that’s how they’re going to do it? No one knows yet.

Several web browsers currently have ChatGPT (or a similar service) built right in, so you can do things like compare the contents of several open tabs at once or ask questions about what you’re reading without having to leave the page. Why isn’t Safari able to do that?

I think Apple’s new writing tools are fine, but they still pale in comparison to what Grammarly offers (which I used to help edit this article). Why is that?

When you consider all that, and add in the existential angst that Tim Cook has had to endure under the 2nd Trump administration, you soon realize that Cook has been having a very bad year… and it’s only getting worse. One theory currently being floated is that instead of trying to play catch-up — a position Apple has rarely occupied — they may try something bolder, such as acquiring ChatGPT competitor Perplexity.

That’s A Wrap

I still have faith that Apple can figure out a way forward regarding AI, one that keeps user privacy front and center while giving us, as Steve Jobs said, things we didn’t know we wanted until we saw them. The pressure has never been more intense, and the stakes have never been higher. At the same time, I fervently hope that everyone at Apple remembers a core philosophy from the Mac’s early days, from a book whose title we saw written on t-shirts at MacWorld Expos in San Francisco: “This is a Mac… It’s supposed to be fun!”

I’ll report on further developments on the future of Apple Intelligence when they are warranted. Until then, I remain…

Your friendly neighborhood Tech Daddy

Many of you have asked if there is a GoFundMe campaign to help us recover from the devastating loss of our home and possessions. The answer is yes! Our dear friend Jenn Melyan has created a GoFundMe for us, which you can access here.

Tech Daddy Substack Founding Members

Leigh Adams
Edgar Johnson
Harvey Rosenfield