Museum educators are well versed in employing multiple techniques for engaging museum visitors. Many use these skills and approaches to support marginalized and vulnerable populations, such as families with an incarcerated adult, families with food insecurity, or unhoused families. Determining how to carry out these beneficial intentions, however, can be challenging. Discovery Museum in Massachusetts, a science-focused children's museum, partnered with a local non-profit organization and a medium security prison to pilot a support program for incarcerated men and the children in their lives. With local and federal funding, Museum educators met with the incarcerated men and created themed activity kits for the fathers, grandfathers, uncles, and brothers to play with during family visits at the prison. Over four years, Museum educators developed meaningful relationships with prison staff, learned the value of listening and persistently offering many types of support, and developed a deep understanding that systemic change is challenging and slow-moving, even with imaginative and determined educators. While quantitative data about improvement in the lives of the men proved difficult to obtain, lessons for educators about how to collaborate with organizations that have opaque and unfamiliar structures, as well as methods for supporting and engaging vulnerable people, are shared.