During the 21st century, more students have been enrolled in U.S. higher education than ever before. These individuals are entering postsecondary education from more diverse backgrounds and with a much broader range of overall goals, values, and skills than their peers before them. As first-year students begin to navigate higher education, they often realize not only the complications associated with the initial separation from family and friends and the need to form new social relationships but also the immense challenges and increased difficulties related to college-level academics. Although the majority of new college students eventually adjust, upwards of one-third of them withdraw or transfer during their first academic year. To complicate matters further, the current generation of college-aged students brings challenges and issues different from those seen in higher education previously. Among them are a shifting focus from knowledge exploration to job preparation, a growing generational gap in technology use between faculty and students, and an increase in mental and emotional health issues. While it is ultimately the students' responsibility to perform well academically and to earn the grades required to progress toward graduation, the university also has a responsibility to provide students with the greatest opportunity for success and to support them along the way. The interventions discussed throughout this article have all netted positive results at Saint Joseph's University (the Rebound Program for eight years, Probation Academic Success Strategies (PASS) for three years, and the satisfactory academic progress communication plan this past year). Each of these initiatives takes human resources to implement, manage, track, and evaluate but can easily be done as part of a full-time employee's job responsibilities. The financial cost of these interventions is minimal, typically only time for employees and the cost of printing and mailing letters to students. The return on investment for helping more students succeed and progress toward graduation is very high.