Reasonable-person psychological detention is an area of criminal law that has been subject to a number of jurisprudential innovations in the 21st century. This work responds to a current gap in the literature regarding the importance of socioeconomic factors to the crystallization of detention in accordance with s. 9 of the Canadian Charter of Rights and Freedoms. The thesis of this paper is that socioeconomic factors are foundational to understanding the social context in which police interactions sometimes crystallize into detention. The socioeconomic aspect of social context reveals the way police interact with individuals in a certain space. Racial aspects of social context are postulated to be tied to socioeconomic aspects insofar as the racialization of individuals tends to occur in certain spaces – namely, high-crime, low-income neighbourhoods. The methodology of this work includes an analysis of trends in detention case law beginning with the 2009 decision of R v Grant and ending with the 2020 decisions of R v Thompson and R c Dorfeuille. Secondly, this work investigates the Honourable Michael H. Tulloch’s Report of the Independent Street Checks Review. Thirdly, this work investigates a series of studies conducted by Yunliang Meng, a geography scholar who analyzed the Toronto Police Service’s racialization of individuals as a function of space. In conclusion, this paper recommends modifications to police practices that require officers to make explicit statements at the outset of interactions with individuals which determine whether or not the individual is detained.