Experts agree that keeping systems up to date is a powerful security measure. Previous work found that users sometimes explicitly refrain from performing timely updates, e.g., due to bad experiences which has a negative impact on end-user security. Another important user group has been investigated less extensively: system administrators, who are responsible for keeping complex and heterogeneous system landscapes available and secure. In this paper, we sought to understand administrators' behavior, experiences, and attitudes regarding updates in a corporate environment. Based on the results of an interview study, we developed an online survey and quantified common practices and obstacles (e.g., downtime or lack of information about updates). The findings indicate that even experienced administrators struggle with update processes as the consequences of an update are sometimes hard to assess. Therefore, we argue that more usable monitoring and update processes are essential to guarantee IT security at scale.