It’s no secret that Cortana, Microsoft’s digital assistant, was a flop in many ways and swiftly disappeared from view following its launch. However, the idea was originally a tremendously ambitious plan that appeared to have all the makings of a fantastic product.
Sandeep Paruchuri, a former product manager at Microsoft, discussed the origins and fate of Cortana in the latest Big Bets newsletter, revealing a few interesting tidbits about the personal digital assistant’s development.
As you may know, the name Cortana is derived from the Halo video game series, in which Cortana is an AI who provides the player with knowledge about what to do next in advance, which is why the name was picked.

However, that was only meant to be an internal codename, and by the time it was ready to debut, Microsoft preferred the name Alyx since it was simpler to say. However, as the name Cortana became well known, fans pressured Microsoft to use it, and the name stayed.
That was until Microsoft‘s then-CEO, Steve Ballmer, attempted to change the name once more. Ballmer wanted the function to be integrated with the rest of Microsoft, particularly the Bing search engine, therefore the name Bingo was chosen. Thankfully, Satya Nadella took over as CEO of Microsoft soon after, and he allowed Cortana to keep her original name.
However, the name changes are only one of the fascinating details in this story. Cortana began as an ambitious effort by a tiny team who intended to build a real-life assistant who was proactive like the Cortana character in Halo, according to Paruchuri. As time went on, more people were involved, but as time ran out, some features had to be removed in order to meet the deadline.
If you had an appointment on your calendar for a specified time, Cortana was meant to show up and notify you when to start driving, taking traffic into account, so you could arrive on time. That did not turn out to be the case. Cortana was also notably released as a US English-only feature, which alarmed several members of the development team.
Cortana was released alongside Windows Phone 8.1, and it received positive feedback from those who were already lovers of the platform, but things went worse after that. After the initial favourable response to Cortana, every product manager at Microsoft wanted a piece of it, according to Paruchuri. With multiple employees attempting to implement different features, every decision necessitated lengthy meetings, and Cortana’s feature set began to lose her initial emphasis. Furthermore, a slew of AI-related features began to bear the Cortana moniker, obliterating Cortana’s original purpose.
Microsoft also wanted to bring Cortana to the desktop, which it did with the release of Windows 10, but it wasn’t really useful given that most desktop PCs lack microphones. Most PC users weren’t used to installing a Microsoft account to their computer at the time. Cortana, like Windows Phone, faded into oblivion once Windows 10 was released, as it wasn’t really helpful on the PC, and Android and iOS users had superior built-in options. Cortana is nearly completely gone in Windows 11, and it’s now only a business feature.
It’s always fascinating (and a little depressing) to learn about the mistakes that lead to a product’s downfall. More information on the story can be found in the most recent Big Bets newsletter.