This dissertation examines trans people's relationship to policy in Montréal and Toronto. Adopting a critical/reflexive methodology, it begins by examining how past research has been framed through the object of study of gender transgression (transness). It demonstrates that this focus has limited the scope of policies considered: which policies are discussed, what is said about them, and how they are evaluated. In order to move forward, the dissertation proposes the concept of policy encounters, that is, contact between policy users and policy. This notion is developed by examining trans people's encounters with housing, social assistance, refugee, and trans-specific policies (e.g. civil status). Based on 30 one-on-one interviews, this review expands the scope (breadth and depth) of what is considered in relation to trans people and policy, uncovers new points of evaluation, and re-examines political priorities. All in all, policy encounters offer a much better perspective of trans people's policy landscape than gender transgression. Finally, this dissertation highlights the skills and strategies adopted by trans people to navigate complex and imperfect policies. As a whole, the project moves towards offering policy advice to policy users.