One preferred embodiment of the present invention provides a system and method for evaluating the performance of an inter-messaging network of voice mail systems. This preferred embodiment includes an evaluation test unit that connects to the inter-messaging network and requests a test data file to be retrieved from a particular voice mail system in the inter-messaging network. The requests for the test data file are generated according to a schedule of operation so that the requests are repeated within a defined time span. Accordingly, the performance of the inter-messaging network, as represented by the result of the request attempt, is evaluated according to a defined level of performance, such as a preferred time limit. Other systems and methods are also provided.