Going into wilderness with loads of goods that is just asking to be raided in post-apocalyptic world, when they are not escorted by lots of hired mercenaries.

Assigning poor settlers as suppliers seems wild. It should rather be by robots that could be constructed!

Bug: By the way when assigning a settler in sanctuary to supply pit stop, then the supplier does not use the gate entrance. The Pit stop is surrounded by a junk fence with a gate at the far end, and the supplier with the brahmin does go close to the wall and disappears and then reappears right in the middle of the settlement.