Relocating and starting a new life in a foreign country may entail a constellation of new stressors for Haitian immigrants; thus, research that enhances our understanding of how this vulnerable population contextualizes migration-related stress is necessary. The objectives of this study were to: (a) identify what factors are associated with migration-related stress, and (b) describe which and why specific migration-related stressors were most significant from the perspective of those suffering from high migration-related stress post migration via the stress proliferation lens of the stress process model. In this mixed-methods, sequential, explanatory pilot study, first-generation Haitian immigrants (N = 76) were recruited to operationalize migration-related stress, using the Demands of Immigration Scale (DIS). Participants (n = 8), who scored 25 or higher on the DIS, completed an in-depth audio-recorded follow-up interview that consisted of open-ended questions and a stressor-ranking questionnaire. Descriptive statistics, Pearson correlations, multiple linear regression (quantitative), and thematic analysis with a double-coded approach (qualitative) were employed to analyze the data. Female gender, older age, English fluency, and migration after the age of 18years were associated with higher migration-related stress. However, only gender and English fluency predicted migration-related stress. In interviews, participants ranked five migration-related stressors as most stressful: language barriers, financial strains, loss of social networks, family conflicts, and exposure to discrimination/stigma. A nuanced depiction of migration-related stressors and proliferation mechanisms of migration-related stress may help identify areas where support and preventive efforts should be directed to improve social integration, stress levels, and mental well-being among immigrants.