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Hey ProjectWill, I can't progress with Taile ("Go at night to Dusk to begin the attack on Jenpachi") and Sheila ("We need to boost Sheila's morale, go to the mainstreet at evening"). Their events won't trigger for me. Do I miss something here? Otherwise it seems to be a bug. 

(+1)

Do you happen to have the priority feature active?

I did in fact. :D I wasn't sure what the purpose of that feature was and clicked on it. I turned it off again and the events trigger now.