The invention concerns a system and method of predicting problematic dialogs in an automated dialog system based on the user's input communications. The method may include determining whether a probability of conducting a successful dialog with the user exceeds a first threshold. The successful dialog may be defined as a dialog exchange between an automated dialog system and the user that results in at least one of processing of the user's input communication and routing the user's input communication. The method may further operate such that if the first threshold is exceeded, further dialog is conducted with the user. Otherwise, the user may be directed to a human for assistance. In another possible embodiment, the method operates as above except that if the probability exceeds a second threshold, the second threshold being higher than the first, then further dialog is conducted with the user using the current dialog strategy. However, if the probability falls between a first threshold and a second threshold, the dialog strategy may be adapted in order to improve the chances of conducting a successful dialog with the user. This process may be cumulative. In particular, the first dialog exchange may be stored in a database. Then, a second dialog exchange is conducted with the user. As a result, a second determination is made as whether successful dialog can be conducted based on the stored first exchange and the current second exchanges. This cumulative process may continue using a third and fourth exchange, if necessary.