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I have visited Ruth however the quest has yet to update. I have tried various ways to solve this problem like quitting and rebooting the game and starting a new save. However these attempts all failed and I am now stuck. Is this a bug or am I just playing wrongly?

Yeah I have also had this issue. Got the grades to 100 and completed every questline as far as I can but the "placeholder ending" never happened. Not sure if there is  anything else to do.

I think we are not on the same page but still hopefully the creator fixes both problems so that me and you also including all player that are facing these problem can experience the game better.

 

Have you read the deleted files on the headmasters computer? Check the recycle bin.

Well this is the problem here, I have already finished this quest once. However, due to my clumsiness, I overwritten that save. Now I wish to replay the game but I could not get the staff mission about Ruth to update. Since this is happening, I could not vote to change the rules in the Friday meeting session.

If you've started a new game it will reset everything you done so that shouldn't make a difference . Where exactly are you stuck? Make sure to follow the quest log. 

It did not reset everything tho. First, The new save doesn't have the old headmaster quest, but I didn't care that much about it. Then there is my main problem, in order for me to progress further I would need to finish two staff quests. I have finished Sally's quest and now I am left with Ruth's. However, I have talk to Ruth and I am already left with no conversation option, yet the quest didn't update. Because of this, I cannot gather information to blackmail her. 

I have added your discord and I will be asking questions there since our conversation does have some spoilers. my username is USVY in discord.