By examining the differences in the influence of contextual factors in the relationship between acculturative stress and psychological distress among Latinas from Mexico, Puerto Rico and Cuba, this study seeks to advance culturally sensitive social work practice with Latina clients. Using the National Latino Asian American Survey, the study included Latinas born in Mexico (N = 257), Cuba (N = 264) and Puerto Rico (N = 118). Analysis consisted of (i) one-way Analysis of Variance, (ii) Scheffe post-hoc test and (iii) multi-group path analysis to examine country-of-birth differences in relationships between contextual factors, acculturative stress and psychological distress. Discrimination remained a key factor in acculturative stress and psychological distress among all Latinas. An increase in age was associated with higher psychological distress for Cuban-born Latinas and an increase in familismo was associated with decreased psychological distress for Mexican-born Latinas. Content with the decision to move to the USA and years in the USA impacted on the acculturative stress of Cuban- and Mexican-born Latinas. The implications are that macro and micro long-term social work interventions targeting discrimination among Latinas are essential to their well-being and that country-of-birth differences suggest a need for further research focusing on Latino subgroups’ experiences with acculturation to inform effective social work policy and practice that targets the unique needs of Latino subgroups.