The phrase "shift left" has become a cornerstone of modern security thinking—encouraging teams to catch and fix issues earlier in the development lifecycle. But is early always better? In this session, we’ll challenge the overreliance on shift-left strategies and explore what happens when security theory meets real-world complexity. From legacy systems and third-party code to overwhelmed developers and business pressures, we’ll look at why shifting left isn’t always feasible—or effective. Attendees will walk away with a more balanced, practical approach to building security in continuously, rather than relying on a one-size-fits-all solution.