Dust boot assemblies for providing grease relief while preventing or minimizing infiltration of contaminants into a cavity in the dust boot and between the surfaces of a greased joint coupled to the dust boot. Some such dust boot assemblies include two-piece grease relief inserts having a body and a shield, wherein the body includes grease relief route(s) and the shield prevents or minimizes infiltration of contaminants into the grease relief route(s). Other dust boot assemblies include one-piece grease relief inserts with integral body and shield components. Some grease relief routes include axial and radial channels. Grease relief inserts are inserted under an edge of a dust boot. A dust boot skirt covers grease relief ports through which excess grease is relieved to the external environment. The grease relief insert is located to in a portion of the dust boot experiencing limited or zero movement.