This article explores the complexities involved in calling for a boycott to be imposed on Israel. It distinguishes core immorality that justifies boycotting a state and indirect reasons for a boycott. The core Apartheid immorality in Palestine –encapsulated in the notion of a Jewish state – is argued to be inequality of stake in the political community. This core immorality is the past, present and future operative cause of multi-layered, and temporally related, manifestations of immorality, namely occupation, dispossession and discrimination. Not only a boycott that is phrased too narrowly, but also a sincere but socially premature boycott can entrench core immorality. Inspired by John Rawls's political philosophy, but also seeking to extend his vision, the argument here defends an analogy between civil disobedience and a boycott. Both rely on the likelihood of success in bringing about social and moral transformation. This transformative potential is canvassed in relation to Israel.