The Morehead-Cain Scholarship at UNC at Chapel Hill has a Civic Collaboration Summer for rising sophomores, and five scholars were assigned to work with Maryland Philanthropy Network and the Middendorf Foundation. This study looks to explore both the permit and grant processes from the perspectives of nonprofit organizations, foundations, and the Baltimore City Government. By interviewing various stakeholders, the scholars gained insight and understood just how complex these processes were. All sides provided their experiences, which led the scholars to develop key takeaways and recommendations to create a more efficient system.