There once was a virtual assistant named Ms. Dewey, a comely librarian played by Janina Gavankar who assisted you with your inquiries on Microsoft’s first attempt at a search engine. Ms. Dewey was launched in 2006, complete with over 600 lines of recorded dialog. She was ahead of her time in a few ways, but one particularly overlooked example was captured by information scholar Miriam Sweeney in her 2013 doctoral dissertation, where she detailed the gendered and racialized implications of Dewey’s replies. That included lines like, “​​Hey, if you can get inside of your computer, you can do whatever you want to me.” Or how searching for “blow jobs” caused a clip of her eating a banana to play, or inputting terms like “ghetto” made her perform a rap with lyrics including such gems as, “No, goldtooth, ghetto-fabulous mutha-fucker BEEP steps to this piece of [ass] BEEP.” Sweeney analyzes the obvious: that Dewey was designed to cater to a white, straight male user. Blogs at the time praised Dewey’s flirtatiousness, after all. 

Ms. Dewey was switched off by Microsoft in 2009, but later critics—myself included—would identify a similar pattern of prejudice in how some users engaged with virtual assistants like Siri or Cortana. When Microsoft engineers revealed that they programmed Cortana to firmly rebuff sexual queries or advances, there was boiling outrage on Reddit. One highly upvoted post read: “Are these fucking people serious?! ‘Her’ entire purpose is to do what people tell her to! Hey, bitch, add this to my calendar … The day Cortana becomes an ‘independent woman’ is the day that software becomes fucking useless.” Criticism of such behavior flourished, including from your humble correspondent.

Now, ...