Self-placement in math is becoming increasingly popular in community colleges in the U.S., where students will decide for themselves whether to enroll in non-credit developmental (or remedial) math courses. To fully understand the factors associated with students' math enrollment choices and the long-term effects of initial math enrollment choices, we use data from all first-time-in-college students in the Florida College System to conduct a multinomial logistic regression analysis and an inverse-probability regression adjustment analysis. We find that most students chose to directly enroll in college-level math, with significant differences by gender and high school math preparation. First-year math enrollment choices were significantly associated with likelihood of passing college-level math and the number of college credits by the third year.