Guest Stars Clark Gregg as Arthur Sackler, Sr. Jack Mulhern as Tyler Kryger Brian Markinson as Howard Udell Sam Anderson as Raymond Sackler Ana Cruz Kayne as Brianna Ortiz Ron Lea as Bill Havens Carolina Bartczak as Lily Kryger John Ales as Dr. Gregory Fitzgibbons Noah Harpster as Dr. Curtis Wright Matt Baram as Dr. Robert Kaiko Johnny Sneed as Dr. Tim Cooper Jonathan Higgins as Dr. Coyle Co Starring Olivia Markowski as Toddler Kaylee Vivienne Markowski as Toddler Kaylee David Tompa as Conference Room Lawyer Darrin Baker as Dr. Hartman Natalia Gracious as Dr. Cooper's Receptionist Joy Jamaal Grant as Shawn Flowers Kafi Pierre as Nurse Erin Tara Samuel as Diane Shnitzler John Bydevaate as Mechanic #3 Kyle Gatehouse as Riggs Bryan McLelland as Mechanic #1 Helen Taylor as Joan Pharmacist Kathryn Bellamy as Tanya James Boyd as Mechanic #2 Laura Afelskie as Jess Brewster Stephanie Herrera as San Juan Nurse #2 Nicco Lorenzo Garcia as Lab Technician Sekyoung Lee as Pharmacist #1 Jack Fagan Reslinski as Teenager #2 Stuart Dowling as Lewis Richard Lam as Eager Doctor Ian Deakin as Wailing Patient Rafferty Blumberg as Teenager #1 Marvin Karon as Dr. Morris Tarah Consoli as Event Coordinator Hume Baugh as Reggie Terrel Mollison as Cashier Robbie Randy Morgan as Commercial Director Amy Hawke as Dr. Morris Receptionist Gregory Yeo as Pharmacist #2 Elena Reyes as San Juan Patient Brillette Barreat as San Juan Another Patient Andres Jaramillo as San Juan Nurse #1 Patricia Mislan as Dr. Gregory's Receptionist