While terribly inconvenient, in a way it must be flattering that your transition went so well someone looking at old photos of you still can't believe you ever once lived as a different gender.
It is such a good feeling. One time I showed my ID to get a hotel room and the receptionist politely told me my boyfriend had to actually be here, I couldn't just use his ID. He got so awkward when I explained we were the same person, it was delightful!
LinkedIn has a tendency to flag gender changes on accounts for similar reasons, but unlike Uber, they just request paperwork proof. It seems likely that either Uber’s HR chatbot was programmed by, or its termination criteria were set by, non-trans men; as (in the Western culture where Uber is based) women are often familiar with fighting with name change problems, and (in all cultures) trans people are accustomed to being flagged by machine algorithms for transitioning.
