A system and method for using a client-side hypervisor in conjunction with a secure network-side monitoring mechanism to detect removable media insertions since a client's last network session with the secure network is presented. The hypervisor uses a “client-side insertion value” to track the number of times that a user inserts removable media into a socket located on the client. When the client is connected to the secure network, the client's hypervisor notifies the secure network of each insertion and the secure network increments a “secure network-side tracker value.” For each login request, the client includes the client-side insertion value, which the secure network compares against its secure network-side tracker value. When the two values are different, the secure network sends an action request to the client, such as a request to perform a full system scan. Once the client performs the action, the client's hypervisor resets its client-side insertion value and attempts to logon to the secure network again.