An anchoring device, system and method. The anchoring device, system and method can include one or more rolling hook devices designed to couple or be secured to a projection such as those associated with rooftops. The rolling hook devices can include an arched member and any number of wheels to facilitate positioning. The rolling hook device may further be coupled to one or more tethers that allow it to serve as an anchor or work in conjunction with any number of other devices that function together as an anchoring system.