I killed the caravan before summoning the drider just to make things easier for when I pass the Harper house & side with them. But after summoning the drider I cannot roll to intimidate or deceive, the conversation will just end & when I speak to the drider again the same conversation will occur & still can't roll to make him walk with my party but I can easily click the attack option.
My only options are to keep the caravan alive until we reach the Harper house & then side with the harpers or to straight up just randomly attack someone while you are walking with the caravan & drider. Obviously not a game-breaking bug but just found it somewhat annoying bc I like to kill my enemies slowly so bigger battles are easier.