I passed it, luckily.
Here's what I think should be done to pass it:
1. You have to get out of prison through phone call to Boris;
(Meet Cellmate in the showers where she gives you a card with the phone number, then call in Interrogation Room)
2. You have to pull the Junction Box lever twice in the Interrogation Room(I did that on different days, but maybe you can do it at one day); Then you have to meet Cellmate in the showers(may take few days for that) and talk to her there, then Warden will come and you have to kick him in the groin to go to the Punishment Cell; There you need to meditate and you'll get out of Prison to The Gym, like nothing happened;
3. You have to get to Insexity location(Dream Stairs?) and click the door to your apartment(I don't know if can you do it from the Gym or not, but I did it from the Punishment Cell); Also you need to have seen Eva and Ashley in the mirror in your apartments Bathroom, so when you go back to work after all this previous steps, you'll see that Anna is now the Receptionist.
4. Now wait for Saturday or Sunday, then go out on the street and you'll get a call from Anna to meet at the Club, there you'll watch and click through the event; And I belive like that you finish the Prison part of the game.
P.S.: Hope that helps.
