This article addresses the uneasy tensions and overlaps between race, sexuality, and citizenship, by focusing on the moments when queer diasporic people of colour slip “in” and “out” of Pride Toronto—the organization that hosts the annual Toronto lesbian, gay, bisexual, transgender, and queer Pride Parade. Drawing on Pride Toronto’s thirtieth anniversary promotional material, released in 2010, and the organization’s 2002 five-year strategic direction plan, the author applies a queer feminist diaspora reading practice to problematize how the documents, taken together, presents Pride’s queer history in Canada, which continues to be narrated by the organization in ways that de-racialize queer subjects and invoke white gays and lesbians as central to its story. Pelau MasQUEERade, a Caribbean queer diasporic group that participates in the Pride Parade, reveals how the histories of queer diasporic people of colour are strategically appropriated and belatedly visible only in sporadic moments in the documents. Pelau MasQUEERade’s presence works to disturb normative accounts of Pride, while simultaneously opening the door to overlapping histories of queer diasporic people in the event. The group reworks Pride Toronto’s de-racialized narrative of sexuality by gesturing to the ways in which race, sexuality, and notions of citizenship operate in multiple and contradictory ways.