As a marketing nerd who likes to give unrequited and unwarranted opinions, I think Microsoft missed a massive opportunity with Cortana. Rather than quietly canning her — which essentially screamed “we failed” — they should have leaned into the narrative and spun it into a strategic evolution. They could have said Cortana was getting a major upgrade or even a “reverse lobotomy” to become the new Copilot. That would’ve framed the change as growth, not defeat — a bit like what Apple did with Siri, just without saying it out loud. Siri’s still there, just smarter, better integrated. Microsoft could’ve done the same, but with a wink.
And for a bit of fun — to humanise the transition — they should’ve added a bit of tongue-in-cheek lore that hinted Cortana was a distant relative of Clippy. A cheeky line buried in the user experience — an easter egg: “It runs in the family” or “Productivity is in her paperclip-shaped DNA.” People love a callback and they sure love nostalgia, and that kind of storytelling would’ve turned a phase-out into a moment of brand personality. Instead, they just… deleted her. Master Chief would have been so disappointed.