Play day two two times again but ask about crownus to all puppets and if Jestyn wants to follow you choose the "no" option. It'll likely give you more intel on the lore and yes it is necessary to play day two two more times and forcefully try to enter crownus's room on both days, also remember to also ask each pupet thier relationship with the others. Im unsure how many times you must play day 2 but if you follow what I told you to then you will get that ending.