Punitive welfare conditionality, combining tough sanctions with minimal self-directed support, is a defining feature of contemporary UK working age social security provision. This approach has been justified by policy makers on the basis that it will increase the numbers in paid employment, and thereby offer savings for the public purse that are also beneficial for individuals who are expected to be healthier and better off financially as a result. In this article, we aggregate two qualitative longitudinal studies (Welfare Conditionality, 2014–17; and Lived Experience, 2011–16) that document lived experiences of claiming benefits and using back-to-work support services. In both studies and over time, we find, contrary to policy expectations, that coercion, including sanctions, was usually experienced as unnecessary and harmful and that poverty was prevalent, both in and out of work, tended to worsen and pushed many close to destitution. Conditionality governed encounters with employment services and, perversely, appeared to impede, rather than support, transitions into employment for participants in both studies. These constitute ‘shared typical’ aspects of lived experiences of welfare conditionality. We propose Combined Study Qualitative Longitudinal Research as a new methodological approach to extend inference beyond the usual study-specific confines of qualitative generalisation.