In this article, Michael Dumper critically examines his engagement with the Middle East peace process from 1992 through to 2023. He provides an overview and a discussion of some of the key issues and the contribution played by Track Two discussions, particularly in relation to Palestinian refugees and Jerusalem. The section on Jerusalem explores in more detail the difficulties in finding a mutually agreeable framework for the management of the holy sites in the city and considers the approaches of some of the groups participating in these discussions. The author also reflects on the cultural and educational influences that guided his participation in these discussions and some of the pitfalls he failed to avoid. The way in which academia is coopted into policy making is also considered. The conclusion offers both some lessons learned and a prognosis for the prospects of a negotiated agreement.