This article assesses the effectiveness of de-radicalization efforts in Israel’s prison system. Israel’s prison population contains a representation of “security prisoners”, which can range from anywhere up to 40%. The Israeli prison de-radicalization process is not so much a program as it is a suite of measures which aim to quell the challenges associated with prison environment as well as comply with international law – permitting an inmate organizational structure to communicate with authorities, allowing family visits, and providing education opportunities. The article assesses that if the effectiveness of Isreali prison de-radicalization efforts is based on recidivism rates as the key performance indicator, then efforts would be deemed as a failure. A key lesson that can be drawn from Israel’s de-radicalization efforts however is that it is possible, indeed recommended, to treat inmates—regardless of their level of radicalization—in a dignified and humane manner. However, Israel’s ability to significantly de-radicalize security prisoners is limited if it is at all existent in its current form. Security prisoners with the potential for positive change should be placed in a different, perhaps foreign setting. It is suggested that candidates for de-radicalization are segregated from their peers, held in special prisons or separate sections within a prison, and their families provided with the necessary setting and protection by authorities, any de-radicalization initiative will most likely fail.