While there is a lack consensus as to whether orientations for online students should be completed on campus or online, research suggests that having an in-depth orientation and onboarding process increases the academic preparedness of online students and, consequently, improves retention. This action research study attempted to evaluate the effectiveness of an in-depth, virtual, student orientation on the retention and academic preparedness of online students at a small, private college. There was an increase of 7% in the retention rate from the fall to spring in the year the institution implemented the online orientation. Additionally, the results indicate students felt more academically prepared, a finding also supported by the results of a faculty survey. While the number in the sample was small, the results are promising and signal a need for additional research on the link between a formal orientation, retention, and academic preparedness for online students.