I believe it's you unknowingly softlocked it by doing the hacking and you forgot to tell Anna about it on the same day or even on the same week. For example, you hacked Adrian's computer on Thursday and you have to tell Anna immediately in the Kitchen. However, I assume maybe on that day you did something else and forgot until the next week. That may be the reason why you didn't trigger the dialogue of telling Anna about Adrian.
Because for me, I too once hacked Adrian's computer on Thursday, forgot about it but still able to told Anna about it on Friday ( the same week ).
As for sharing River with Josef, it's pure RNG but it's only available if you chose River Slut Route. Just invite River into your Room on Friday and have sex, whether Josef come or not is the RNG.