Guest Stars Timothy Granaderos as Montgomery De La Cruz Josh Hamilton as Matt Jensen Mark Pellegrino as Officer Bill Standall Steven Weber as Principal Gary Bolan Michele Selene Ang as Courtney Crimsen Bryce Cass as Cyrus RJ Brown as Caleb Brenda Strong as Nora Walker Joseph C. Phillips as Greg Davis Anne Winters as Chlöe Rice Wilson Cruz as Dennis Vasquez Ajiona Alexus as Sheri Holland Steven Silver as Marcus Cole Chelsea Alden as Mackenzie Samantha Logan as Nina Jones Allison Miller as Sonya Struhl Sosie Bacon as Skye Miller Kelli O'Hara as Jackie Cindy Cheung as Karen Dempsey Jake Weber as Barry Walker Jackie Geary as Amber Foley Co Starring Brandon Butler as Scott Reed Richard Gross as Judge Campbell Anna Zavelson as May Dempsey