Grow Your Own Programs (GYO) have gained increasing popularity with the impact of shortages of quality teaching candidates in many school districts, particularly in urban areas. To address the lack of quality teaching candidates, school districts and states have responded creatively to recruit the best teachers for their schools. To explore some of the intricacies involved with GYO partnerships between school districts and universities, this article describes a case study of how two urban school districts partnered with a local university to provide pedagogy and support for paraprofessionals' Grow Your Own programs and their processes to build the partnerships. Specifically, it highlights the overall impressions, opinions, and feelings of stakeholders about participating in the program and the specific incidents, obstacles, and occurrences that may provide guidance and a first attempt at "best practices" for other organizations that might consider GYO programs.