Many racialized immigrants, particularly Caribbean immigrants, leave their countries in hope of attaining a better life in Canada. In addition, skilled immigrants are lured to Canada by an aggressive immigration policy which promotes the notion that there is potential for immigrants to improve their lives and succeed as well rounded citizens who contribute to the Canadian society (Teelucksingh and Galabuzi, 2005). However, when many racialized immigrants try to enter the Canadian labour market, they face various challenges which sometimes continue after finding employment. This study will address the concerns relating to the barriers that Canadian labour market policies can present in the labour market, and the ways in which some Caribbean immigrants understand the policies, and experience its impact through systemic barriers. With the use of interviews by key informants from the Caribbean community, this paper seeks to explore the ways in which some racialized immigrants are acutely affected by Canada’s labour market policies.