A management server communicates with an authentication server that authenticates endpoints, which are configured to connect wirelessly with access points (APs) controlled by respective ones of a plurality of controllers. Weights for the APs and the controllers are stored. Event logs detailing requests for authentication of the endpoints are received. For each request, roaming conditions for the endpoint that triggered the request are determined. Also, a respective weight of one or more of the AP connected with the endpoint and of the controller that controls the AP is increased by a respective amount depending on whether the roaming conditions are caused by the AP and the controller being improperly configured or properly configured. Identities of ones of the APs and the controllers having weights that exceed one or more weight thresholds each indicative of an improperly configured AP or controller are stored.