A method and system for retransmitting messages using an alternate mode of communication when an original mode of communication is determined to be unsuccessful. A message is first transmitted using a connectionless-mode of communication such as by using an Internet electronic mail message. A request for acknowledgment of receipt of the message and/or individual operators within the message is requested. If the acknowledgment of receipt of the message is not received within an appropriate time determined based on an urgency level of the reply, the message is retransmitted using a more reliable mode of communication such as a connection-mode of operation which includes a direct telephone connection over a public telephone network using a modem, using an ISDN line, or a cable with a cable modem.