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The transformation of the Gamaa Islamiya can be understood by analyzing it against Argyris and Schon€ ’s double-loop learning model. This paper bases the analysis on five books published by the Gamaa Islamiya, which include comprehensive elaborations on internal reflections and criticism of Al-Qaeda. While the Gamaa Islamiya’s learning can be framed with the model of double-loop learning, Al-Qaeda’s reactions can be depicted as a less evolved single-loop learning system. This case is relevant for the discovery of key mechanisms of deradicalization that could be used as a blueprint for other groups.