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...