For many students, the path to earning a postsecondary educational degree is often met with personal and social obstacles, but first-generation students are less likely to even enroll in postsecondary education and they have a higher probability for attrition when compared to their counterparts. The purpose of this study was to examine the relationship between delayed enrollment, regional wealth, and first-generation status on community college student success. This study analyzed differences in student success for students who enrolled at the community college immediately after high school graduation, for those who delayed enrollment up to two years, or delayed enrollment more than two years. This study further explored whether regional wealth had a significant relationship with the rate of delayed enrollment among first-generation and non-first-generation students. In particular, the study examined whether there was a non-causal relationship between enrollment status (immediate enrollment, short-term delay, long-term delay), regional wealth (as measured by the composite index in five service regions), and first-generation status (first-generation or not). The findings from this study revealed that students who immediately enrolled had higher student success ratios when compared to students who delayed enrollment up to two years. In addition, students who graduated from high school in the most wealthy region had the highest student success ratio when compared to students who graduated from high school in the least wealthy region. Additional tests revealed if a student graduated from high school in the least wealthy region, the probability of delaying enrollment more than two years was approximately three times more likely than for students who graduated from high school in the most wealthy region. There was a significant interaction between enrollment status and regional wealth with student success whereas the students who immediately enrolled had significantly higher student success ratios when compared to students who delayed enrollment up to two years for both the least wealthy region and the most wealthy region. There has recently been an increase in the number of empirical studies examining the precollege characteristics that affect the academic success of first-generation community college students. The results of previous studies combined with the current study could have important implications for administrators who develop interventions or provide the resources to help first-generation students over-come many of the challenges they face. These studies can support community college leaders in their efforts to increase student academic achievement and graduation rates. More specifically, it would be advantageous for leaders to fully understand the different educational impacts on students who immediately enroll or delay enrollment at two-year institutions. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]