According to aspects of this disclosure, a monitored person, via an end-user computing device, may generate a rule deviation request and send the rule deviation request to the computing system of the supervising agency. Based on the received request, the computing system may, upon receiving an indication that the request is authorized, determine a reconfigured rule and enforce the reconfigured rule. In some instances, the computing system may be configured to suppress an alert that would have been generated based on an activity prohibited by initial rule but that is permitted by the reconfigured rule. The reconfigured rule may remain in effect for a duration specified by the request. In this way, the techniques may increase the efficiency with which rule deviation requests are processed and enforced.