I asked for additional crew to follow me around in a tavern and he did but came unarmed so maybe you could look at that.
Yes in the tavern, and when we left the tavern he arrived unarmed. He was still unarmed at the next location. I can send you the save game if you like.You mean you hired a character found in the tavern to join you as a shore crewmember?
@Jack Rackham rewrote some things for equipping land crewmembers a while back. Did the guy not auto-equip on the next location reload or so?