When trying to manually transfer an item from one container/hand/slot to another, you can't move an item from a container/item of clothing to one listed above it by using LT, you have to use RT and scroll it down until it comes back around to the top. EXAMPLE:
FIELD VEST
CCU JACKET
PATROL PANTS
MT BAG
In order to move an item from the CCU jacket to the field vest I would WANT to hold A on the item, and press LT to the field vest and release. However you can't. You are forced to hold A on the item and hit RT, RT, RT, RT, then release A.