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No more than 200-word Abstract (190 words): In the last two decades, an emphasis on servant leadership has led modern institutions of higher education to create programs embracing the needs of the communities in which they are immersed. Establishing a servant leadership agenda that also involves prisons is not always seen as a priority by contemporary academic administrations. This is in part due to internal policies used to discriminate against student applicants with criminal history records, making it difficult to justify a service that would somehow involve offenders. This often happens in spite the fact that the servant leadership ideal does not subordinate to any meritorious clause. The main objective of this presentation is to describe a number of successful strategies to initiate Inside-Out courses and to discuss the Inside-Out within the servant leadership philosophy making sure that all students (both inside and outside students) become agents of change in our communities. In addition, the presentation also focuses on how university imposed constraints to the delivery and implementation of Inside-Out courses can be used with creativity to design engaging courses and develop additional extra-curricular activities that would benefit the university, the prison, and the community as a whole.