Abstract: A computer implemented system and method of allocating costs of wireless telephone usage. Billing and usage information is received from at least one wireless telephone service provider related to calls made and received by a plurality of wireless telephone service users. Each call is automatically categorized as a business call or a personal call based on at least one of a phone book, time of day, day, and preset flag associated with a given telephone number. A categorization policy may also be applied in the event call categorization cannot be completed. The categorized calls can be reviewed via a graphical user interface and modification of a categorization can be effected. A final categorization of the calls is ultimately approved, which then allows charges to be appropriately allocated to users, and/or to/from a pool of available wireless time.