In the Italian prison reality, the school activities of every order and degree have been guaranteed by law since the end of the 70s of the last century. The present contribution intends to stimulate a critical reflection on the dimensions of educational action in complex social situations such as that of prison. He wants to offer an opportunity to rethink paths and tools of educational planning in relation to the use of new training methodologies, such as the theatrical methodology in its different modalities and its specific styles. It is difficult to satisfy the needs of treatment, orientation, social integration and re-education and at the same time develop formal knowledge. The active and participatory methodologies of the theater can be useful for the change of the context of life.