Even before he took office, USAID’s new administrator, Mark Green, made public his conviction that the objective of foreign assistance “should be ending its need to exist.” He acknowledged the sentiment was not new. Indeed, his predecessors—from administrations of both parties—related a similar doctrine. But Green pledged to make to make the tenet the “core operating principle” of the United States’ largest aid agency. And in articulating plans to pursue “strategic transitions,” he lent new import to an age-old question and resurrected a serious discussion within the international development community about when and how USAID should seek to transition select middle-income partner countries away from traditional grant-based assistance toward alternative forms of engagement. This paper seeks to inform USAID’s approach to strategic transitions by offering 1) a review of lessons learned from past USAID transitions and mission closures as well as similar efforts undertaken by other bilateral aid agencies; 2) an assessment of the advantages and drawbacks of using quantitative benchmarks to identify countries for transition, as well as an illustrative framework for evaluating countries’ transition readiness; and 3) a selection of tools and approaches the US government can leverage to create a path for sustained country engagement.