Patching software theoretically leads to improvements including security critical changes, but it can also lead to new issues. For System Administrators (sysadmins) new issues can negatively impact operations at their organization. While mitigation options like test environments exist, little is known about their prevalence or how contextual factors like size of organization impact the practice of Patch Management. We surveyed 220 sysadmins engaged in Patch Management to investigate self-reported behaviors. We found that dedicated testing environments are not as prevalent as previously assumed. We also expand on known behaviours that sysadmins perform when facing a troublesome patch, such as employing a range of problem solving behaviours to inform their patching decisions.