Explore a comprehensive analysis of system administrators' software update management practices in this USENIX conference talk. Delve into the five-stage process administrators employ for updating multiple machines, examining the unique challenges and considerations they face. Gain insights from a survey of 102 administrators and in-depth interviews with 17 professionals, uncovering limitations in existing procedures and organizational influences. Learn about the difficulties in acquiring meaningful update information, effective testing and deployment, problem recovery, and navigating management dynamics. Discover proposed research directions and community actions aimed at enhancing the efficiency of system administrators' update processes, ultimately contributing to improved organizational security at scale.