This dissertation examines the ways in which a specific social and linguistic field around the sex trade shapes access to and experiences with health and social services for transgender and cisgender women and non-binary sex workers and experiential people in Winnipeg, the capital city of the Midwestern Canadian province, Manitoba, on Treaty One. It is the result of over 5 years of ethnographic engagement with sex worker rights activists, services providers, stakeholders and public and private events, meetings and discussions focused on sex trade political action and reform, and 52 in-depth interviews with workers, experiential people and stakeholders. The sex workers and experiential people I spoke to asked plainly for service providers to do better in terms of caring for them and meeting them where they are, highlighting the need for specialized services that are tailored to participants’ priorities and lived realities. The findings also call for the general training of service providers that addresses the complexity of the sex trade, the principles of harm reduction, and anti-racism. Beyond strict and sometimes mandatory categories of experiences in sex work and the sex trade, there is a need to recognize individual experiences, goals, and the harms they might identify in their lives. Grounded in extensive ethnographic field data, my results also reveal the complex field of power relations that play out in the sex trade industry in Winnipeg, and how these power relations get enacted through various linguistic deployments to structure the conditions of access to social and political support networks and resources. I argue that the redeployment of linguistic signifiers, such as “sex worker”, “sex trade worker”, “sexually exploited person”, “prostituted women”, “human trafficking survivor”, open up a polarizing moral field that people have to navigate to get their health and social services needs met. This turbulent and irreconcilable social field is an effect of what I refer to as deliberative identities. I use this concept to go beyond dominating and restrictive dichotomies—as either ‘empowered’ or ‘victims’—that too often populate public health, health policy and media representations of sex workers, their bodies, their agentive capacities, and their social positionings.