The study provides new information on the relationships between students’ socioeconomic backgrounds, utilization of college enhancement strategies, and subsequent 4-year college enrollment. Enhancement strategies represent student behaviors used to bolster the competitiveness of a college application, such as Advanced Placement exams and a variety of extracurricular activities. By drawing on two national datasets that span the 1990s (NELS) and the 2000s (ELS), the study uncovers how these relationships have changed during a period marked by escalating demand for college and growing class inequality. The findings provide partial evidence of class adaptation (Alon in Am Soc Rev 74:731–755, 2009) based on the combination of increased use of multiple enhancement strategies (“high overall use”) among higher SES students and increased influence of high overall enhancement strategy use in predicting college enrollment, particularly selective college enrollment. Implications are discussed in terms of the higher education system and pervasive social inequality.