Abstract: A button assembly that couples and releases a hitch insert to and from a hitch is described. A button of the button assembly may be configured to be pressed to a degree that allows the hitch insert to be inserted into and removed from a hitch. However, the button assembly may be configured to prevent a user's finger (or other extremity) from entering an aperture of the hitch insert that accommodates the button. For example, in a pressed orientation, a surface of the button that a user contacts may remain flush (or substantially flush) with an outer surface of the hitch insert.