From the Editor’s Desk: The AI Hallucination No One Talks About (Premium)

You may have seen the story over the weekend about Microsoft killing support for Cortana in Windows 10 and 11. This should come as no surprise as the software giant has been stepping back from its personal digital assistant for years: among other moves, it killed off its Cortana mobile clients and deprecated Cortana in Windows 11 in 2021.

The reaction to this news is interesting to me and it speaks, I think, to a growing frustration in the Windows community that Microsoft just never seems to try hard enough to succeed with products and services that deserve better. Here, Windows Media Center and Windows Phone are obvious examples, but Cortana deserves a spot on this list too: after all, Microsoft is one of the few companies on earth with the backend capabilities to make this kind of thing work. (The other two being Amazon and Google, the market leaders.)

But we shouldn’t act surprised: Cortana never had a good mobile play, which is how Google Assistant rose to prominence. And with its nearly nonexistent presence in the consumer market, Microsoft never really made a big push with smart speakers and other peripherals as Amazon did with Alexa. Businesses were predictably uninterested in letting users talk out loud to their PCs, and we’ve all seen the viral videos of Cortana yelling at people when they first turned on their Windows 10 PCs, an absurd problem for computer labs with multiple PCs.

Looking at it more broadly, Cortana was never strategic to Microsoft. It started off as a feature of Windows Phone 8, limiting its exposure to users, and then Microsoft killed Windows Phone, limiting its exposure even further. And Cortana, like live tiles, was a feature that made more sense on mobile than it did on PCs. And so most users simply ignored it on PCs. And then so did Microsoft, understandably.

But you don’t have to be a computer scientist to see the similarities between Cortana and other personal digital assistants and what Microsoft is now promoting with AI. Indeed, it’s impossible not to view AI—in Windows, in particular—as a natural evolution of what it did previously with Cortana. You could stretch the definition of AI a bit and include other previous efforts like Bob, Clippy, and that insipid search dog in Windows XP as part of a continuum of ideas that led us to Windows Copilot this year.

Windows Copilot, we’re told, is “integrated into all of Windows.” It can answer questions. It can take actions on your PC. And it can do things with documents, including creating summaries. And this limited set of features will be extensible by third parties, which is what makes Copilot a platform.

That’s all very neat, but it’s also disconcertingly familiar: Cortana could answer questions, too. It could take actions on your PC, like launching apps. It could integrate with your Microsoft or Work/School account, remind you about appointments and meetings, and help you create new ones. What it lacked is that document functionality and, now, extensibility.

Cortana supported both voice and typed interactions, which makes sense to me, and while I’m sure Copilot will too, eventually, the initial demos we’ve seen are all typing-based, which seems like a bit of a step backward while perhaps being more natural on a traditional PC. But this is how the Bing chatbot and other AI-based tools on the web work too. I guess the assumption here is that people who want voice control will simply use that more broadly and can thus interact with AI that way as they do with other tasks.

I wonder if the step back from voice is related to the deprecation and now end of support for Cortana and is representative of Microsoft’s desire that we forget this past failure. That is, Microsoft would very much prefer that you did not draw any connection between Cortana and the AI-based Copilot. After all, AI is new. Better. The future.

But it is perhaps instructive to remember that Cortana and its natural language interfaces were the future once too. At the time of Cortana’s introduction, one of its key features was its integration with Bing, ever the also-ran in Search, which Microsoft at the time marketed as a “decision engine.” Which is exactly how it’s marketing Bing today, really, just with slightly different words.

Cortana was originally tailored for phones, so there was a lot of interaction with mobile apps like Maps, Phone, Weather, and so on. Windows Copilot is specific to Windows PCs, of course, so there is interaction with documents and OS features like Dark mode and Focus sessions. Folks, this is the same thing at a high level, and Copilot is just an evolution of what came before it.

Yes, it is also much more powerful, or at least it will be with third-party plug-ins that will work across Bing, Microsoft 365, and ChatGPT. But that’s what evolution means: it’s better, and there’s more to it.

But Microsoft’s shunning of Cortana—a brand that I’ll remind you started as an AI character in the Halo video games that eventually became insane, similar to the “hallucinations” uttered by Bing chatbot and other modern AIs—is interesting when you understand the context. The firm could have continued forward with this brand on Windows, for example, just as it continued forward with Bing on the web despite that brand being associated with defeat. Why didn’t it shun Bing, too?

Simple: Bing is part of a vast network of Microsoft online services that will materially benefit from increased traffic thanks to its similar increased ad revenues. But Cortana was a free feature of Windows that few people used, and improving that usage has no direct benefits. Worse, Microsoft’s Copilot functionality almost certainly will not be free (or at least entirely free) given the expense of AI workloads. Few customers would be interested in paying extra for a feature, Cortana, they had ignored successfully for years. But Copilot might stand a chance.

And so here we are: in with the new, and out with the old. Just pay no attention to the man behind the curtain. Because this time the man is a woman. And her name is Cortana.

Just don’t tell anyone.