Yes you will definately want to run a roller fairlead. Even with a fairlead, I still broke my winch cable last winter and have now upgraded to a Amsteel blue sythentic winch cable, safer stronger and lighter. This winter when it comes time for plowing again, I will go back to my old steel cable that came with the winch. I'm going to cut it down and only use enough to the wrap the barrel of the winch and connect to the plow.