|The U.S. Navy has been trying for many years to automate its personnel assignment process. Periodic assignment of personnel to new jobs is mandatory according to Navy policy. Though various software systems are used regularly, the process is still mainly done manually and sequentially by Navy personnel, called detailers. This paper is a case study in applying cognitive theories implemented via new AI techniques to produce flexible adaptive human-like software. In it we present a sketch of an Intelligent Distribution Agent that aims to largely automate the detailer’s tasks. In particular, we look inside its constraint satisfaction, which is mainly responsible for satisfying the requirements of the Navy’s policies, the command’s needs and the sailor’s preferences in order to achieve “satisfactory” job assignments according to ever evolving Navy standards.