The challenges faced by Caribbean immigrants in America constitute a great perspective in Caribbean literary expression. This work seeks to explore the representation of Caribbean immigrants‘ realities in Nicola Yoon‘s The Sun Is Also a Star and Ibi Zoboi‘s American Street. The question on which this research is anchored is: how do Nicola Yoon and Ibi Zoboi project the situation of Caribbean immigrants in The Sun Is Also a Star and American Street respectively? It is hypothesized that the authors present the conditions of Caribbean immigrants as desperate; despite the surviving strategies and successes that some have. Using Sociocritical and Postcolonial theories postulated by Edmond Cros and Edward Said respectively, this study, reveals that Caribbean citizens migrate to America for better opportunities; but face very difficult conditions in their host country which make very few of them to succeed under hard conditions. The paper highlights the challenges faced by young adult Caribbean immigrants in America and the role of specific cultural dynamics, historical underpinnings, family bonds and other adaptation strategies in their resilience.