The current study examines how the integration of SAT scores with context information about students' neighborhood and high school from the College Board's Landscape™ resource can provide institutions with a nuanced perspective on students' expected performance and retention. This allows institutions to identify incoming students that may benefit from interventions and enhanced academic advising based on easily accessed applicant data. Based on a sample of 188,177 students enrolled at 156 four-year colleges and universities, we examined relationships between SAT scores, Landscape context information, and the SAT in Context to predict first-year academic performance and retention to the second year of college. Results of this study show that: (1) There is a strong, positive relationship between SAT scores and both academic performance and retention to second year; (2) Student neighborhood and high school context information from Landscape moderates SATFYGPA and HSGPA-FYGPA relationships, and in particular, the HSGPA-FYGPA relationship. The added contextual information from Landscape allows institutions to use the SAT and HSGPA more effectively to understand how students are expected to perform and know which students may need more focused support to be most successful; (3) Students with low SAT scores at their college but with top SAT scores at their high schools tended to come from high-challenge environments, and though their HSGPAs may have equaled those of their college peers, these students had lower SAT scores and earned lower FYGPAs in college. Notably, however, these students had above average retention rates despite having below average FYGPAs; and (4) Context information from Landscape was more informative for contextualizing student performance in college than student race/ethnicity. Students from underrepresented groups who come from low-challenge environments enter college with higher SAT scores than do students from high-challenge environments who are not from underrepresented groups. The students from underrepresented groups who came from low-challenge environments also earn higher FYGPAs and have higher retention rates than do students from high-challenge environments who are not from underrepresented groups. When used with Landscape context information and the SAT in Context, SAT scores allow institutions to more effectively identify students who will be successful on campus and those who may benefit from additional academic support as they enter college. Such data can inform important conversations with students about the transition to college to promote students' academic success.