"Hey Copilot" brings back memories of Cortana

Most of you who have used Windows 10 may remember Cortana. It was Microsoft's failed digital assistant for Windows 10 that was clearly inspired by how popular Siri was on the iPhone. The assistant, based on the character of the same name from the iconic Halo universe was given a personality, and Microsoft publicized it rather heavily initially before giving up on it in 2023, after years of disinterest from the general public. In many ways, Copilot on Windows is Microsoft's second attempt at Cortana, but is it making the same missteps as its predecessors?

Case in point is the recent announcement of Copilot Vision in Windows 11 with "Hey Copilot" voice activation. This brought back memories of "Hey Cortana" from 2015, which was a similar wake phrase to use the digital assistant with your voice.

The problem with this approach in general is that the vast majority of people don't really talk to their PCs. On phones, talking to digital assistants makes more sense because it's sometimes easier to talk than type when you're on the go, but PCs (including laptops) rarely benefit from this use-case.

Let's also not forget that Copilot on Windows is also meant for enterprise use-cases, but talking to your PC in the workspace may be too distracting for those in your vicinity and there's also the chance that you'll end up divulging information that isn't meant for anyone other than you.

Then there's also the fact that "Hey Copilot" is clearly geared towards English-speaking customers, and this is the same cardinal sin that Microsoft committed with Cortana. The Redmond tech giant's efforts in this area have historically focused on its U.S. customer base, with little care for anyone else. When it comes to an OS that is being used by hundreds of millions of customers around the globe, this is not a good look. Copilot and AI models trained on English language in general tend to not perform well when it comes to different accents from people who don't have it as their first language.

In most cases, it is actually faster to use your hands to point and type rather than rely on the dictation capabilities of a software. Imagine asking Copilot Vision to "analyze my PowerPoint presentation and generate me a summary" and it ends up doing something completely different altogether, resulting in lost productivity.

Now, I am not saying that voice activation for Copilot is a bad thing - the fact that it's strictly opt-in is good actually. I'm just emphasizing that we've been down this road before and it didn't have a happy ending the last time around. Microsoft had been teasing this feature for a couple of days on X (formerly Twitter) prior to the actual reveal and based on the hype-laden phrasing, it's clear that the company thinks that voice activation is a pretty big deal. But based on Microsoft's own attempt in the past, there is no indication that there is high demand for something like this.

Will Copilot end up dead in a ditch a few years down the line, à la Cortana? Only time will tell, but in the words of Taylor Swift, "I think I've seen this film before, and I didn't like the ending".

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Posted Sunday 19 October 2025 at 4:55 am AEST (my time).

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