A vehicle cargo retaining apparatus and system having a first enclosure with an outer surface and an inner surface. The first enclosure is capable of containing a fluid within the first enclosure, such as to seal the fluid from an external atmosphere. The apparatus and system may further include a plurality of jamming members within the first enclosure and an opening in the enclosure for receiving or removing fluid. In one state, the plurality of jamming members are moveable relative to one another within the first enclosure when fluid is received via the opening allowing the outer surface of the first enclosure to be deformable. In a second state the plurality of jamming members are restricted from moving relative to one another within the first enclosure when fluid is removed via the opening causing the outer surface of the first enclosure to maintain a semi-rigid or rigid state. A control system may control operation of the system to enable the retaining operations.