In an effort to reduce the risk score produced by scanning the environment with Rapid7 InsightVM, I developed a Chef-based automated patching solution for Linux servers. This solution was able to automatically patch most recent versions of Ubuntu, CentOS, Red Hat and Amazon Linux 2 following a predeclared maintenance calendar. Using Ansible, I developed a basic idempotent playbook to deploy the Chef client to machines that weren't running the Chef-client and service yet. Several applications running on deprecated versions of Linux operating systems (SLES 11-13, OpenSuse 11-13, CentOS 4-5) had to be migrated to newer and supported operating systems. Some of the homegrown applications were developed using deprecated versions of Ruby or Perl and had to be updated as well. A few MariaDB databases had to be migrated to newer, supported versions.