This chapter explores the third major peace junction marked by new leadership in Israel and the Palestinian Authority: Ehud Olmert and Mahmoud Abbas. Abbas later described this as the most serious phase of Israeli-Palestinian negotiations. The chapter traces the transition following Yasser Arafat’s and Ariel Sharon’s departures, Sharon’s Gaza disengagement and renewed optimism for peace. Olmert and Abbas introduced pragmatic diplomacy that culminated in the 2007 Annapolis Conference, convened by US President George W. Bush. The conference endorsed a ‘Roadmap for Peace’, requiring Palestinians to unify security forces, dismantle terror networks and promote transparent governance, while Israel was expected to halt settlement expansion, dismantle outposts and ease restrictions on movement. The Quartet would monitor compliance, and Arab states were urged to curb support for militancy. Despite American investment and a structured framework, the process faltered. Persistent mistrust, political instability and recurring violence undermined progress, leaving the Roadmap’s vision of a two-state solution unrealised.