The tragedy of 7 October 2023 left a searing scar on Israeli society, underlined the explosive state of fifty-eight years of occupation of the Palestinian territories and, paradoxically, accelerated Israeli annexation. A day of slaughter by Hamas, followed by months of forced displacement, starvation, destruction and mass killings of civilians by Israel—with genocidal intent if not results—put paid to existing ideas about conflict resolution. On the one hand, there may be no way back after the unspeakable atrocities that have occurred in Gaza. On the other hand, Israel has suffered huge moral and international damage by several legal judgments and a wave of global popular anger. It is also unlikely to become any safer. The complicating factor has been the growing involvement of Iran and the axis of resistance in the problem of occupation, both in supporting Hamas before 7 October 2023 and in launching a multi-front pressure campaign on Israel afterwards. This did not end well for Iran, but the risk is diminished, not gone. The challenge today is to understand how occupation can evolve given Israeli annexationist designs, weak Palestinian leadership and a mix of international neglect and negative involvement, especially from Iran and the US. The essay bundle undertakes this task by means of scenario planning and stakeholder analysis. It seeks to serve as an intellectual resource for conversation that can bring occupation to a peaceful end.