Methods and apparatus involve evaluating endpoint computing assets. The endpoint has both a traditional operating system for applications, and the like, and another operating system during a pre-boot phase of operation. During use, the traditional operating system identifies a last evaluation status of the computing device at a time just prior to shutting down. Upon a next booting, the pre-boot operating system loads and examines [reads] the last evaluation status. If the last evaluation status requires any completion action in order to comply with a predetermined computing policy, either or both the operating systems attend to its effectuation, including communication/handoff by way of one or more security agents. In a variety of ways, effectuation occurs by: determining a present location of the computing device, quarantining the computing device from certain network traffic; VPN enforcement; patching applications; firewall involvement; etc. Computer program products are also disclosed.