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I managed to get Nersmias's conviction at -1 but the conversation continued and when I ended it, I still had to make a "deal" with him for me to talk to Sillan :( 

Did you try leaving the conversation once his conviction reached -1?

I did and it was the same as ending the converation at any other point. 

Although good news! I did manage to reach the 0 conviction result when I tried again with hypnosis and got -11 conviction (and maybe higher trust?)

That sounds pretty strange, perhaps it's a bug. I'll be looking into it next week.

I reviewed the event and didn't see anything strange. However, if Nersmias' trust reaches 0 or less on the same round his conviction reaches 0, you will be locked out of the route to talk to Sillan at no cost.