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Message: <blockquote data-quote="TikkchikFenTikktikk" data-source="post: 5330413" data-attributes="member: 67494">Having just given you general advice on running skill challenges, I've reread your scenario. So let me get more specific:Set very difficult DCs for those skills. Let them fail. Have NPCs suggest that no matter how diplomatic the Paladin tries to be, the timbers won't nail themselves to the gates (for example). At the extreme end, if they fail at trying different things, they fail to adequately prepare the keep. And then they and everyone they know and love dies.This.Give them enough information that they know what they should try, or know who to go to to ask what they should try next. They are new adventurers, so they should be able to fall back on the grizzled veteran, the kindly matron, etc., for advice and instruction.Being veteran veterans and aged matrons, they are likely to give unsolicited advice. Whether the players heed that advice is up to the players.You haven't created a skill challenge. You have created several related skill challenges. Just describing the preparation, you've listed at least five skill challenges that have serious consequences if they fail.I don't see any reason to tell your player's they are in a Skill Challenge. They will be faced with challenges that they must use skills (as opposed to powers) to solve. No reason to be too on the nose about it.Good luck, have fun!</blockquote>