DIYers who work with software often attempt to reuse others’ work wherever they can as they seek to assemble, modify, and extend their systems. In this paper, we briefly discuss the challenges faced by software DIYers in the process of reusing others’ software configurations through our study of the MythTV community. We also discuss the benefits of enabling users to engage with others’ configurations as “gray-boxes,” allowing them to pay attention to just the parts that must be opened up and modified and ignore the rest. We propose a new technical facility called Tailor Wear to give users guidance and hints about where and how to modify configuration artifacts by visually presenting the tailoring traces left by similar or selected peers.