This chapter provides a historical context for the development of gay and lesbian identities in Iceland, emphasizing that this evolution was not a linear or teleological path toward liberation, but rather a contingent process shaped by shifting power dynamics, ruptures, and transnational influences. The chapter explores how Iceland’s legal and medical apparatus, strongly influenced by Danish criminal and medical discourses, played a foundational role in constructing homosexual subjectivity as a site of regulation. Using the 1924 sodomy conviction of Guðmundur Sigurjónsson as a key example, the chapter illustrates how legal and medical discourses worked together to stigmatize and discipline queer existence. It also highlights how transnational exchanges, particularly with Copenhagen, catalyzed the rise of an Icelandic gay and lesbian movement. The founding of Samtökin ’78 marked a moment of localized adaptation of global queer discourses. However, the chapter questions reading legal advancements in the 1990s as unequivocal progress, noting their potential to reinforce homonormativity and neoliberal ideals. Framed through assemblage theory, this chapter critically examines how historical, legal, medical, and cultural forces intersect to continually reconfigure the regulation and normalization of queer life in Iceland.