This design thesis adaptively reuses the former St. Louis County Jail to house an independent living facility and a preschool that incorporates an Intergenerational Learning Center, located in the Downtown Waterfront District of Duluth, Minnesota. Examining how generationally segregated we are as a society and working to bring that back together within a historically preserved building generates a significant portion of my research and design exploration. The unique architectural features of the jail have the opportunity to bring new life and spirit to the building and create a welcoming design in a former place of punishment. The research incorporated in this thesis deals extensively with the existing building in order to protect and promote the character as well as how to stimulate successful interactions between the elderly residents and preschoolers. With neither their pasts nor futures in common, the relationships between these groups exist entirely in the present. The ultimate objective of this design thesis exploration is to implement a program that repositions the building socially from a vacant reminder of trouble into a place people are compelled to be a part of while evolving design standards to provide stimulating and engaging environments for the residents.