I've noticed two issues with the dossiers/social screens.
One is when I had Yakau as my military advisor, but he was still had the "unseen" portrait. If I'm remembering correctly, he agreed to be my advisor without even asking me to do his personal quest - so maybe something in there caused the full portrait not to trigger? EDIT: I managed to have this glitch happen again, and indeed this time I can confirm that it happened while I recruited him on approval alone. 
Second, I'm in a run where I'm engaged to Kxenia and having Vasily as my concubine. All of the Vasily stuff is working perfectly - the change in our relationship status is reflected in his dossier. But there's no acknowledgement of our engagement on Kxenia's dossier. It's shown in the votes screen, though. I also don't have the ability to remove her from her cabinet position or break our engagement. If it matters, I did the villainess proposal option.
