Visions of future computing in residential settings often come with assumptions of seamless, well-functioning, properly configured devices and network connectivity. In the near term, however, processes of setup, maintenance, and troubleshooting are fraught with difficulties; householders regularly report these tasks as confusing, frustrating, and unpleasant. I conducted a series of empirical studies examining both the sources of digital complexity in residential settings well as how people cope with these complexities. Grounded in this fieldwork, I designed a technology probe called Tech Clips. Tech Clips facilitates the sharing of technology-related information by and for people within one's social network. I then conducted a long-term, real-world deployment study in which ten families used the software, while simultaneously completing a series of common computing setup and maintenance tasks. Based on the results of this study, I provide both a rich description of home technology usage and maintenance practices, as well as design implications for software systems that facilitate help-giving between family and friends. The contributions of this research are (1) empirical studies of how lay people understand and cope with vexing technology problems in environments lacking technical experts; (2) the development of a software system to facilitate technical advice sharing; (3) deployment of this system in real-world settings; and (4) recommendations for the design of future tools for facilitating technical help-giving between family and friends.