Every success in TSM depends on your Sim's focus. The game may say your hero has high focus but by looking at the buffs you can see they probably don't. Max out their focus by doing positive buffs to gain longer lasting buffs before doing anything that is task, or quest, or relationship related. I'm wondering if your hero actually has enough positive buffs and very high focus to succeed at this. But there could be an old bug lurking in the game, so maybe a cheat is the way to go. ETA: It wouldn't hurt to have the hero be battle ready by practicing with the sword until they are before doing this one. (higher buffs, battle ready etc., read a good book, had a really good meal other than gruel etc.)
