Principles of the present invention provide techniques for automatically navigating through a telephone menu system. Illustrative techniques of the invention permit a user of a telephone menu system (e.g., IVR system) to record operations needed to navigate to a particular point in a menu tree of the telephone menu system and to either gather information or perform a transaction at that menu point. The information or transaction status may be reported to the user. Part of the act of training may be the association of a command with the navigation operations, after which the automated telephone menu navigation system of the invention will repeat the procedure, in correct synchrony with the telephone menu service, when the user says the command. In addition, the techniques of the invention detect failure or loss of synchronization or changes in the telephone menu.