Forum Discussion
As I explained in my first paragraph, I had raised two levels from Anonymous Ghost to Net Demon to The Oracle while I knew I was stuck trying to get the milestone to register, because I figured perhaps a promotion would cause the game to retrigger the count on the criminal level check for the milestone. I thought because I went to the Anonymous Ghost to Net Demon promotion uncomfortably that maybe something didn't take.
I had been switching aspirations and often going back and forth (as I had been working on my fitness and programming to get the Bodybuilder and Computer Whiz aspiration traits as well and completing other milestone steps). So, I had been moving between aspirations often, and I had the aspiration active for the last promotion, and I am 90% positive I had it active for the previous promotion. I went to the last promotion with a positive moodlet, (focused and playful, and possibly confident) and it still no matter having switched off and back on the aspiration, even after another day at work at the highest level in the career.
At that point, I did the milestone complete cheat to progress the character/aspiration. I saw this was an older issue after a search on these forums but a patch is said to have fixed most of them... Also apologies for necroing a thread earlier yesterday... it was before caffeine and I thought it said March 2019.
Hope this helps