Traditionally, community colleges have been organized in a way that requires students to navigate the college environment without institutional guidance or support. Thus, successful navigation requires knowledge and cultural capital that students from disadvantaged backgrounds, often overrepresented at community colleges, may not possess. The risk of decision-making errors resulting from a lack of knowledge, combined with an overwhelming number of program and course options offered by community colleges, may hinder a student’s ability to successfully enter and persist in a program of study. Indeed, many community college students are confused over college processes and academic trajectories. Recent community college reform initiatives and practices, such as guided pathways and structured transfer agreements, seek to alleviate student frustrations by providing students with more clarity and support throughout their postsecondary experience. Drawing on administrative data tracking over 80,000 community college students in a single state, this dissertation explored various aspects of community college student pathways in order to better understand the impact increased structure can have on student outcomes. Underpinning this research is the theory that clearly defined and educationally coherent pathways into and through programs of study will improve student decision-making, lead to more efficient course taking, and increase student success. However, neither this theory nor the mechanisms by which structure has been introduced have yet been sufficiently tested or evaluated in practice. Among the strategies employed to guide student progression through college is encouraging, and in some cases mandating, early major declarations. The practice is intended to increase structure by defining and exposing students to program expectations as early as possible, thereby leading students to achieve academic milestones in a coherent and efficient manner. However, without sufficient experiences or information, students who are pushed into premature major decisions may be more likely to select into a major that does not reflect their interests or match their abilities, increasing the risk of subsequent major switching. The first chapter of this dissertation sought to understand how, if at all, initial major declaration and major switching were related to student outcomes in a state that required major selection at the time of college entry. After establishing the pervasiveness of major switching among students who selected a program of study at the time of enrollment, I used a competing risks discrete-time hazard methodology to estimate the relationship between major switching and student outcomes and concluded that major switching was associated with an increase in community college degree completion and a decrease in upward transfer. Given the descriptive methodologies utilized, the paper discusses how differential academic and career intents may explain results. Another way in which colleges can increase structure is through the use of articulation agreements—policies that aid students in the transition between 2- and 4-year institutions through course alignment, increased program prescription, and greater access to information. In the second chapter of this dissertation, I employed an instrumental variables technique to estimate the impact of enrollment in structured Associate of Applied Science (AAS) transfer programs on student success. Causal estimates suggested that exposure to such programs had a small positive impact on bachelor’s degree attainment, but did not have any effect on persistence, student course-taking behaviors, community college degree completion, or transfer. One explanation for the small and mostly null findings presented in this chapter may be that the transfer policies ascribed to by AAS programs in the state under review failed to include several dimensions of more ideally constructed structured pathways, such as academic and career advising, the absence of which may have a significant impact on community college students, who often lack sufficient college knowledge to navigate college processes appropriately on their own. Policies focused on increasing structure are often premised upon the idea that the preferred and ideal pathway for community college students seeking a bachelor’s degree includes earning an associate degree, yet little is known about the impact of earning an associate degree on bachelor’s degree completion. Given that the underlying motivation for introducing structure to community college pathways is to increase efficiency and success among students who have historically underperformed, it is important to evaluate whether encouraging students to earn a degree before transfer is a sound policy. The final chapter of the dissertation presents results from a propensity score matching technique used to determine the average treatment effect of earning a pre-transfer associate degree on bachelor’s degree completion. Overall, quasi-experimental results suggested positive apparent impacts of earning the transfer-oriented associate degree (i.e., Associate of Arts or Associate of Science) on the probability of earning a bachelor’s degree. However, no apparent impact was uncovered for degrees in programs typically designed for direct labor market entry (i.e., Associate of Applied Science).