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This study examines how first-generation immigrants in the United States plan for retirement, report income, and engage with the Social Security system. The analysis combines an original anonymous survey of 120 first-generation immigrants with descriptive, correlational, and illustrative aggregate evidence constructed from Social Security Administration, Census Bureau, and related institutional data for 2013–2023. The survey results show three consistent patterns. First, retirement knowledge is limited: most respondents do not understand how Social Security benefits are calculated, yet a large majority would attend retirement-planning workshops. Second, financial behavior is shaped by legal status and labor-market formality. Tax filing rates are high overall, but underreporting incentives are stronger among respondents paid in cash and among groups facing legal or administrative uncertainty. Third, family obligations materially affect long-term planning. Many respondents prioritize supporting relatives over retirement savings, and women report lower earnings despite comparable English proficiency and, in this sample, higher educational attainment. Over 2013–2023, Social Security program income and program cost rose alongside the immigrant population, but this aggregate exercise is illustrative only, is not causal, and cannot identify immigrants’ net fiscal impact on the system. The paper’s main contribution is therefore behavioral: it shows how limited knowledge, payment formality, and family obligations shape retirement planning within a non-representative regional sample of first-generation immigrants.