A communication management system in which a work machine communicates with an outside of the work machine, the communication management system includes: a work machine including: a communications carrier setting unit configured to set a communications carrier that provides a communication service to generate information about the set communications carrier as communications carrier information; and a communication unit configured to transmit the communications carrier information to the outside of the work machine; and a communication state analyzing unit configured to gather statistics on the communications carrier information included at two or more different times among pieces of the communications carrier information transmitted from the communication unit, the statistics gathering being performed for each of the times.