Guest Stars Hettienne Park as Tamika Collins Summer Fontana as Maya Maitland Scarlett Blum as Jessa 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 Shannon Mayers as Duty Sergeant Taj-Naranja Jenkines as Inmate Brandon O'Dell as TBD Jennifer Christa Palmer as Shirley Jackson Derek James Jones as C.O. Body Search Jaxon Moore as June Moore Margo Moorer as Mary Mason Ira Carmichael as Supervising C.O. Max Bickelhaup as Tom Yates 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