In recent years, there has been a significant increase in the number of students with disabilities seeking postsecondary education. The complexity of needs is also increasing, resulting in more students withdrawing from college or taking leaves of absence in their first year. In 2012, the Student Academic Support Services office (SASS) at McDaniel College piloted "McDaniel Step Ahead," a five-day transition program that aims to fine-tune the academic, social, and independent living skills of first year students with disabilities. As a result, there has been a notable increase in the number of students with disabilities still in active status at the end of their first year. The early connection with SASS and McDaniel resources creates a natural venue for early detection and intervention. This practice brief describes the implementation of "Step Ahead," the needs addressed by "Step Ahead," the data collected from past years, and the implications and challenges for planning future years.