The purpose of this article is to critically explore pre-existing and continuing welfare conditionality of NEET (not in education, employment, or training) experienced young people in the UK. The article traces the policy history of NEET over the last 25 years, to demonstrate the enduring nature of benefit sanctioning that NEET experienced young people have faced throughout a decade of austerity, Brexit, and now the COVID-19 pandemic. The article engages with key narratives from 43 interviews of NEET experienced young people and youth work professionals, undertaken prior and during the pandemic. Overall, the article argues that government actors and policy makers alike have not gone far enough to support NEET experienced young people. The article found that more structural and institutional levels of support from central government are needed to meaningfully engage NEET experienced young people in their education, employment, and training trajectories throughout periods of crisis.