A system for compliance monitoring of a user of a monitored location is provided. The system includes at least one checkpoint monitor installed in the monitored location and a system server at a monitoring center being configured to be in communication with each checkpoint monitor via a network. Each checkpoint monitor includes a checkpoint server and being configured to monitor access to the monitored area. Each checkpoint monitor is configured to perform an authentication process to authenticate both an assignment status and an activity status of a user and transmit the resulting data to the system server.