Cart control systems and methods of controlling cart caster direction allow for operation of carts near walls without caster jamming. Cart control systems comprise a cart with one or more swivel casters, a wall, and a guide surface proximate the wall that is configured to swivel outwardly at least one of the swivel casters to be directed toward the wall when the swivel caster traverses the guide surface in a direction substantially parallel to the wall. When the caster is directed toward the wall, the floor contact of the caster is further away from the wall than the swivel axis of the caster and generally under the cart. When reversing direction, the caster swivels outwardly, with the floor contact remaining further away from the wall and generally under the cart. Thus, the caster does not swivel into the wall and jam the cart.