The aim of this issue is to provide readers with a better understanding of the inexplicable connection between school, community, and incarceration, and how better prepared professionals can make a difference in the lives of youth in the school-to-prison pipeline (STPP). This issue provides readers with an awareness of the current status of the STPP and suggests the advancement of quality professional development (PD) research and practices. First, a brief historical perspective is provided on deinstitutionalization in special education. The argument is made that special education institutions of the past are eerily similar to juvenile justice (JJ) facilities of today. The contention is that JJ institutions and the STPP are evolving in a similar manner as special education did more than 40 years ago, providing the field with a cautionary tale filled with a sundry of potential and pitfalls. Then, a brief description is provided with regard to the characteristics of those in the STPP and those incarcerated. Connections are made to educational and civil right legislative mandates. Finally, each article in this issue is introduced. The articles are presented in the context that quality PD for the professionals who work with students along the STPP continuum can and do transform the lives of disenfranchised youth.