International social work associations lack sufficient guidance to address tensions within social work education, employment, and registration about individuals with criminal convictions. This tension arises from the need to uphold social work principles of human rights and social justice while minimizing the risk of harm to clients. Limited research exists on how social workers with criminal convictions navigate the profession. Until 2019, when data were collected for this study, there was no information on the topic in Aotearoa, New Zealand.This article reports on an exploratory qualitative study of individuals navigating the social work profession with a criminal history. We aimed to determine whether participants faced discrimination and whether this impacted their careers. An interpretative phenomenological analysis was applied to data collected in 2019 through 11 semi-structured interviews with registered and nonregistered social workers with one or more criminal convictions.Participants’ experiences highlighted an overarching theme of once a criminal, always a criminal, showcasing discrimination experienced by social workers with criminal convictions when pursuing a social work career. This overarching theme was underpinned by four predominant subthemes relating to stigma and oppression.Participants’ experiences add to evidence that some practices within social work clash with the profession’s underpinning principles. The authors argue that social work associations, registration bodies, educators, and employers should understand the value people with lived experiences of the criminal legal system can bring to the profession and facilitate supportive access to social work careers as they are representative of populations served by the profession.