A system and method for initiating a telephone call to a telephone line that is connected to a modem and an answering machine, the modem being configured to connect to the telephone call prior to the answering machine, determining whether the modem has connected to the telephone call, determining, if the modem has not connected to the telephone call, whether the answering machine has connected to the telephone call and providing a first indication to a user if neither of the modem nor the answering machine has connected to the telephone call.