A communication processing system is coupled to a global computer network. At least one inmate communication from an inmate is automatically converted into an inmate digital communication for communication to at least one remote device. The at least one inmate communication is received at the communication processing system from a correctional facility. At least one side of each of the at least one inmate communication is automatically scanned into at least one digital file. The at least one digital file is automatically converted into the inmate digital communication according to at least one sending template. The at least one sending template is based, at least in part, on at least one formatting requirement of at least one of: the at least one remote device, and a service provider of the at least one remote device. The inmate digital communication is electronically communicated to the at least one remote device.