Historically, retaining students and maximizing their academic achievement has been a challenge for administrators in American colleges and universities. Since the mid-twentieth century, the sophomore year has increasingly been suspected of being a gateway to declining grades, decreased morale, and increased attrition among college students. During the twenty-first century, this dynamic has worsened, in part due to the national movement of freshman year experience programs which has deferred students' attrition and achievement issues to the sophomore year; there is also conjecture that these trends may be amplified or altered by the shifting demographics in the composition of students attending college, with notable increases among women and Students of Color. Regardless, there has been little research conducted regarding the sophomore year experience, and how it differs from the experiences of students enrolled in other years in school, especially for students of different genders or races. This study examined the sophomore year experience through the lens of the student development theory, identified as tasks. Additionally, the study examined if student development tasks could predict academic achievement of sophomores as compared to underclass and upperclass students regarding cumulative grade point averages, both immediate and long-term. Finally, the study was intended to identify which student development tasks could predict retention of sophomores. In this study, an institutional sample of 469 students was solicited from a large university in the northeastern United States. The randomly selected sample completed a web-based instrument, The Student Developmental Task and Lifestyle Assessment, to assess levels of behaviors and attitudes associated with student development tasks; data was then grouped according to students' year in school, race, and gender. Using a number of statistical analysis (Multivariate analysis, Regression analysis, Univariate analysis, and Same sample/group t-test analysis), the connectivity among the variables, and extent of their influence were determined. Several important findings emerged. Most importantly, clear developmental differences, as defined by the SDTLA, constitute a sophomore year experience and syndrome, different from the experiences of freshmen, junior and senior years. This is based in part on a decline in engagement in Cultural Participation during the sophomore year, as compared to the freshman year. Additionally, six interrelated developmental tasks form two behavioral clusters related to autonomy and relationships; these can sometimes exist in mutual conflict, leading students to make forced choices where fulfillment of one developmental task occurs at the expense of another. Furthermore, the significant tasks and subtasks of the sophomore year flat-line (from the freshman year) leading to a sense of stagnation where forward momentum may feel compromised in comparison to the freshman year. It is also important to note that student development tasks served as predictors of academic achievement for sophomores, as it did somewhat consistently for other students groups, usually involving the subtasks, Academic Autonomy and a set of interchangeable variables regarding relationships. These results mirrored and re-enforced the effects of tasks and subtasks associated with the sophomores' profile of engagement. Together, these elements and the sophomore profile of engagement mirrored a low-grade malaise often identified as the sophomore slump or syndrome. Finally, groupings of other students demonstrated that the sophomores' profiles of engagement most likely vary, particularly by race, and gender, although these differences are not unique to sophomore students only. The implications of this study are discussed, focusing on student affairs-led interdepartmental and intentional programming initiatives, sophomore year learning communities, a sophomore curriculum focused on Intergroup Dialogue, and sophomore developmental advising. In sum, this study contributes to the previously referenced and limited literature addressing the sophomore year experience, as an issue for higher education administrators today. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]