This article details the evolution of Yemen’s prison deradicalization program, through the initial Yemeni Committee for Dialogue, and the constant challenges that seem to plague deradicalization efforts. It is a descriptive account of many aspects that are responsible for the ineffectiveness of the Yemeni effort, such as a lack of serious political will and commitment, the trend of former participants leaving the program to go on and conduct attacks abroad (with a significant Yemeni population at Guantanamo Bay) and issues around knowledge of effective implementation. The article even raises some scepticism that efforts to rebuild Yemen’s program is largely designed to get many from US officials. One option has been to link into Saudi Arabia’s deradicalization efforts even though that too has problems with recidivism.