Conducting qualitative field research involving drug users within a politicized criminal justice setting presents a unique set of ethical, legal, and safeguarding concerns and quandaries for researchers. There is a paucity of qualitative research with community-based drug-using offenders who form part of the UK Government (England and Wales) criminal justice strategies (Senker and Green; Hucklesby and Wincup). Hodgson, Parker, and Seddon highlighted this group as an emerging study population. This article aims to provide a more recent contribution covering the difficulties of accessing and researching with a hard to reach and politicized criminal justice drug-using population, such as risks of re-traumatization, risk assessment, safeguarding, criminal disclosure, and personal safety. The first author reflects on her research from her own unique political position as a policy advisor to the UK Government on criminal justice drug policy, with a view to providing recommendations for research with a hard to reach and hidden population who represent a marginalized group. The combination of reflexivity in research and the use of Interpretative Phenomenological Analysis as a research methodology proved helpful in addressing and overcoming some of these ethical, political, and other quandaries.