In this paper, we investigate how many iterations users are willing to tolerate in an iterative Frequently Asked Ques- tion (FAQ) system that provides information on HIV/AIDS. This is part of work in progress that aims to develop an automated Frequently Asked Question system that can be used to provide answers on HIV/AIDS related queries to users in Botswana. Our system engages the user in the question answering process by following an iterative interaction approach in order to avoid giving inappropriate answers to the user. Our findings provide us with an indication of how long users are willing to engage with the system. We sub- sequently use this to develop a novel evaluation metric to use in future developments of the system. As an additional finding, we show that the previous search experience of the users has a significant effect on their future behaviour
