This study examines whether strategies commonly used by high school students for enhancing their chances of gaining college admission may contribute to social inequality in postsecondary education. Comparisons are made between nationally representative samples of high school seniors across two decades, from the early 1990s to the early 2000s. The analyses identify the extent to which students’ SES was associated with the use of admission-enhancing strategies, determine the extent to which the relationships changed across a two-decade period, and examine the role of academic achievement in this process. Results confirm that higher SES students are more likely to employ admission-enhancing strategies than lower SES students, but more importantly that this gap widened over time. These findings suggest that admission-enhancing strategies may be partially responsible for maintaining socioeconomic disparities through education.