Though a large percentage of U.S. students enter higher education with mathematics deficiencies, many institutions allow these students to decide the timing of their enrollment in developmental mathematics courses. This study of 3476 first-time-in-college students entailed the review of student outcomes (Fall GPA, Fall-to-Spring retention, Fall-to-Fall retention) for those who enrolled in developmental math during their first semester compared to those who delayed enrollment. The findings suggest that policy requiring mandatory enrollment during the first semester for developmental math students may be in the best interest of students and their institutions. (Contains 5 tables.)