Don't forget Cortana going rampant in the middle of that timeline and Cortana both gaining and losing a direct Bing brand association. That will forever be my

Don't forget Cortana going rampant in the middle of that timeline and Cortana both gaining and losing a direct Bing brand association. That will forever be my favorite unforced error in Microsoft's AI saga: the cheekiness of directly naming one of their AI assistants after Halo's most infamous AI character whose own major narrative arc is about how insane she becomes over time. Ignoring the massive issues with consumer fit and last minute attempt to pivot to enterprise, the chat bot parts of Cortana did seem to slowly grow insane over the years of operation. It was fitting and poetic in some of the dumbest ways possible.