This inquiry explores how college students’ family communication environments affect their adjustment during the first year of college in two different cultures: Belgium (n = 513) and the United States (n = 431). Three structural equation models were tested to define the moderating effects of (a) perceived family support, (b) quality of academic advice from parents, and (c) quality of social advice from parents on associations between family communication patterns (FCPs) and student adjustment. Although most relationships are more complicated than predicted based on FCP theory and inquiry, various patterns emerge across models and populations. Conversation orientation tends to foster positive adjustment for both cultures while conformity orientation promotes negative adjustment for Belgian students. In addition, perceived family support and advice quality moderate several relationships between FCP and academic self-efficacy, college stress, and loneliness. Differences between the two cultures, theoretical implications for FCP, and practical implications for academic counselors are debated along with future inquiry avenues.