Issa Rae Gives Update on ‘Insecure’ Season 4 Issa Rae is one busy woman. She is currently promoting HBO’s Lady Sketch Show. She eased the stress of her ‘Insecure’ fans when she announced that the writers are finishing up season 4. They will start shooting ‘Insecure’ in September. Fans will also get 10 episodes instead of the usual 8 episodes. How did you feel about season 3? Are you excited for season 4?