Growing up, Kristal watched nearly every man in her life disappear to prison. She channeled that struggle into keeping families connected, both as a social worker and with her van service that drives families to visit loved ones in far-off prisons. But when Kristal's dad and brother return to Philly, her happiness meets the realization that release doesn't always mean freedom. Passionate, funny and resilient, Kristal remains determined to carve out a different future -- for herself and for her young nephew, Nyvae. Part observational documentary, part family album, A Woman on the Outside is a tender portrait of one family striving to love in the face of a system built to break them.