This article focuses on the evaluation of transfer from Track Two diplomacy to negotiations and policymaking by examining four Track Two initiatives between Israelis and Palestinians over the issues of water and Jerusalem. The article first discusses the transfer process for the water and Jerusalem cases and then presents lessons drawn from the comparative study. The comparative assessment reveals similarities concerning transfer in terms of what the contributions of Track Two are to the process of negotiations, which transfer strategies are used, and what conditions are necessary to make a contribution to the outcome. Initiatives in both cases employ primarily the strategy of working with influential people and they are more successful in impacting the process of negotiations rather than the outcome. Their contribution to the process of negotiations shows regularities in the types of learning acquired and used. Successful transfer to outcome is observed in one occasion when transfer strategies were implemented effectively, the negotiators were open to outside information, and there was political willingness. Asymmetrical transfer of people, and of ideas, from Track Two initiatives to negotiations was a barrier to effective transfer. © The Author(s), 2009.