HBO Ending Insecure With Season 5 ✖ Insecure will end with Season 5, which is headed for production and slated to premiere on HBO, later this year. HBO renewed Insecure for Season 5 last May, alongside the premiere of Season 4. It shouldn't be all that surprising to fans of Issa Rae's hit show to hear that Season 5 will be the end; the story arcs of Insecure's ensemble of young black characters have been spiraling toward the finality of adult lives and choices. Given where Season 4 left things, it makes sense that Issa Rae is ready to bring things to a close with a fifth and final installment, and go out on her own terms.