My first job, I was in-house at a fur company with this old pro copywriter, Greek, named Teddy. And Teddy told me the most important idea in advertising is “new”. Creates an itch. You simply put your product in there as a kind of calamine lotion. But he also talked about a deeper bond with the product: nostalgia. It’s delicate, but potent.
– Don Draper (Mad Men Season 1, Episode 13 – “The Wheel”)
I was reminded of this Don Draper quote from one of my all-time favorite TV scenes – the Kodak Carousel pitch – when reflecting upon my contrasting feelings about iOS and iPadOS 26 a few weeks ago. Some of you may be wondering what I’m doing here, starting my annual review of an operating system with a Mad Men reference. But here we are today, with an eye-catching iOS update that, given the circumstances, is betting it all on the glittering allure of a new visual design, and a tablet operating system that comes full circle with old, almost nostalgic functionalities repurposed for the modern age.
I’ve spent the past three months using and working with iOS and iPadOS 26, and there’s this idea I keep coming back to: the old and new coexist in Apple’s software strategy this year, and they paint a hyperrealistic picture of a company that’s stuck in a transition phase of its own making.
From a software perspective, Apple didn’t exactly have a great 2024 or beginning of 2025. And personally, I certainly didn’t kick off the year thinking that by September, I’d be happily working from my iPad Pro again. But let’s take a step back in time for a second, shall we?
In hindsight, Apple’s 2024 was characterized by an unusually vaporware-adjacent presentation of AI features at WWDC that were meant to change the narrative surrounding the company’s lackluster progress in artificial intelligence. As pressure mounted from regulators on one side (the DMA saga also kicked off last year) and Wall Street on the other, there we had a roster of executives on a virtual stage reassuring us that Apple wasn’t behind on AI; in fact, they had been waiting to ship a version of AI that was far more useful – and far more integrated – than the chatbots we’d seen to date. To be fair, it looked great! And thus the mission was accomplished. The online discourse was steered away from the “Apple is falling behind on AI” discussion and onto a more hopeful, quintessentially Apple angle: the AI made by Apple was going to be late to the game, but better than everybody else’s…eventually.
It was a beautiful moment of optimism, while it lasted. As the rest of 2024 rolled on, it became clear that the promise of Apple-developed Foundation models with on-device AI, Private Cloud Compute, and a Siri knowledge graph integrated with App Intents was maybe going to be more of a 2025 affair. Meanwhile, the few Apple Intelligence features that the company did manage to roll out landed with a big thud. Image Playground performed like a generative AI model from three years prior. Notification summaries got the company in hot water with the BBC and other news organizations, forcing them to pull the feature. (Spoiler alert: it’s back in iOS 26.) Siri was redesigned for Apple Intelligence…without actually being more intelligent. It’s ironic that what was considered by many (including yours truly) the “best” feature of Apple Intelligence – its ChatGPT integration – often performed worse inside Siri than in the ChatGPT app itself.
And that’s Apple Intelligence alone. One of the key hardware/software additions to the iPhone 16 lineup – the Camera Control button – arrived in an incomplete and confusing state. And I probably don’t need to rehash the story again, but while all of that was happening, iPadOS had been seemingly forgotten by Apple, left lingering in a hybrid not-an-iPhone-but-also-not-a-Mac state that failed to justify the existence of the M4 iPad Pro and all of its untapped power. While I was ultimately able to work around the limitations of iPadOS to get all my work done on the iPad Pro, I – and other longtime iPad users – began 2025 wondering whether we’d be better served by macOS after years of disappointment in the iPad’s wasted potential.
There was a lot riding on Apple’s software strategy in 2025. Now that we’re entering the final phase of the Apple product launch year, I believe that, in hindsight, their three key moves from the first half of 2025 are – at least from a marketing perspective – the best approach they could have followed.
First, the new AI Siri features were officially delayed to “the coming year”, and at WWDC, executives explained why they needed more time than anticipated to get them right. Then, Apple unveiled a new design language that – to varying degrees of success – unifies its user interfaces across platforms. Finally, the company embraced the iPad’s modular nature with a complete reimagining of the device’s software in iPadOS 26, borrowing from the decades-long traditions of macOS to bring new windowing and multitasking features to the tablet. You have to hand it to Apple PR: that’s a pretty effective marketing strategy to, once again, steer the public conversation and attention to a place that’s more comfortable for Apple.
But my reviews aren’t about marketing; they’re about the reality and everyday practicality of using these operating systems. Beyond the renewed promise of Apple Intelligence and a future version of Siri, what is it actually like to use the new AI features shipping in iOS 26 today? Once the novelty of Liquid Glass wears off, does the new design meaningfully improve our interactions with apps? Is iPadOS 26 truly the miracle answer to all of our iPad woes that we thought it could be at WWDC?
These are the questions I hope to provide an answer to with this review. You can always look at iOS and iPadOS as reflections of Apple’s trajectory throughout the years, and that’s more true than ever in the OS 26 release cycle. These operating systems tell the story of a company in the middle of its own internal transitions – with new roles for executives and several new devices on the horizon – that is also sitting quietly while the rest of the tech industry is transitioning to AI-infused software everywhere.
My goal this year is to tell the story of these two operating systems, explain what they represent in this moment in time for Apple, and evaluate them for what they accomplish.
Let’s dive in.
