The consistent academic underperformance of students from diverse backgrounds is a national concern and the subject of study by numerous researchers. Some scholars suggest this underperformance indicates teacher lack of preparation to address the needs of a highly diverse student population (Hollins & Guzman, 2005; Ford, 2008; Darling-Hamond, 2004). Central to the overall efforts for improving achievement outcomes should be a focus on the educational experiences of the segment of population that is underperforming, namely students of color, from diverse cultural and linguistic background. Policies of immigration are particularly relevant for the students who are immigrants to the United States or are the first generation born in the United States, given that these policies directly impact their social security and stability, potentially altering their educational experiences. This exploratory study employed a multiple case study methodology (Stake, 2006) framed within critical theory (Carspeken, 1996) focused on how students experience and negotiate their parent being ordered deported and in what ways their schooling experiences are impacted by the threat of parental deportation in one of the largest Cape Verdean immigrant communities in Southeast New England, the community of Brockton, Massachusetts. Participants for this study were purposefully selected through the Consulate of the Republic of Cape Verde. Three youth participants, their parents and 3 community leaders were interviewed using Seidman's (2006) three series interview format, and using Madison's (2005) six types of question variations. Data was collected in the form of participant interviews, document analysis, participant and community observations, and field notes. Data analysis was done using Madison’s (2005) five level of analysis. The findings of this study highlight the impact of immigration policies on youth and the importance of school districts that serve large immigrant populations developing structures responsive to the issues of immigration, addressing teacher ideologies in professional development and teacher preparation programs.