Increasing the conditionality of welfare benefits is a growing trend in many developed countries, particularly in relation to some groups who may be perceived as undeserving of state support. Problem drug users (PDUs) are one such group, and in the UK most PDUs do not work and a high proportion claim benefits. Facilitating the movement of these individuals into employment is a policy aim, because it is believed to improve the circumstances of drug users (and promote future abstinence) and because moving all groups off benefits and into work is a primary purpose of recent welfare reforms. Yet little is known about the interactions of PDUs with the UK benefits system or how recent moves to increase the conditionality of benefits are likely to affect this vulnerable group. This paper begins to address this gap by exploring the perceptions that PDUs and relevant frontline staff have of drug users’ interactions with the welfare system and the factors affecting their prospects for employment. The findings suggest some aspects of recent welfare reforms, notably the simplification of benefits, may help PDUs interact with the system. However, the data also reinforce claims that the increased use of sanctions is unlikely to succeed in improving employment rates amongst this group without intensive support and demand-side interventions.