Systems and methods for caster obstacle management

In various embodiments, a caster assembly may include a wheel rotatably coupled to a caster housing and a deflector tab pivotably coupled to the caster housing and offset from an outer wheel circumference for use in moving or traversing obstacles encountered during wheel movement. In some embodiments, the deflector tab may include at least one retaining element configured to hold the deflector tab in a pusher position or allow movement of the deflector tab into a ramp position. In the pusher position, the deflector tab may push a mobile obstacle in front of the wheel motion. In the ramp position, the deflector tab may facilitate moving the wheels over a fixed obstacle.