Guest Stars Hettienne Park as Tamika Collins Scarlett Blum as Jessa Maitland Summer Fontana as Maya Maitland Michael Esper as Kenneth Hayes Joshua Whichard as Ollie Peterson Michael Hyland Cole as Herbert Parker Frank Deal as Fred Peterson Claire Bronson as Joy Peterson Co Starring Sir Brodie as Don Harrier Jennifer Christa Palmer as Shirley Jackson Margo Moorer as Mary Mason Derek James Jones as C.O. Body Search Taj-Naranja Jenkines as Inmate Jaxon Moore as June Moore Brandon O'Dell as TBD Ira Carmichael as Supervising C.O. Max Bickelhaup as Tom Yates Shannon Mayers as Duty Sergeant Barry Victor Piacente as Teacher's Conference Speaker Swift Rice as Jonathan Hughes Yasmein Ziyad as Dee Dee Moore Duncan E. Clark as Frankie Peterson James House as Umpire Cody Reed as Jimmy Zerrick Williams as Larry Nneoma Nkuku as Willow Rainwater