In supplies, can you pick up (or if a Specialist, Extract) a second Supplies box if you're already holding one? I'm assuming you'd drop the first one, but don't know if you actually can...?
What it could not do is carry both at the same time, unless it has Baggage... ITS Season 12 v.1.1; Page 51: Each Model can carry a maximum of 1 Supply Box. As exception, Troopers possessing the Baggage Special Skill can carry up to 2 Supply Boxes. ... but I don't find anything that prevents from taking one, dropping it, and then taking another. (Edit and add) On the other hand, there is nothing that explicitly allows it. In these cases I would recommend an agreement between players