Abstract: Since the end of the 1967 Six Day War, successive Israeli governments - both Labor and Likud - have actively promoted or passively allowed settlement construction in the West Bank and Gaza Strip. Increasingly, however, many Israelis are coming to see the settlements as a major obstacle to lasting peace with the Palestinians, and as the linchpin of questions about the character of the Jewish state. The following monograph explores the legal aspects of a possible future evacuation or relocation of some Israeli settlements and settlers from the territories. The monograph reviews the existing legal framework in the territories and explores the multi-layered complexities of the law of the land. It distinguishes between areas annexed to Israel proper and non-annexed areas. The paper further distinguishes between the possibility of physical evacuation, and severance of the legal connections among the settlers, the land, and the land's structures. Finally, the paper addresses the question of fair compensation for settlers and concludes that any compensation would best be disbursed by a body created through primary legislation.