This study follows Alaskan students in their first six years after high school to describe the pathways they took to postsecondary education and careers. Analyzing data from multiple national and state education and employment sources, the study examines the trajectories of 40,000 students who exited public high schools in Alaska from 2004/05 to 2007/08. The analysis shows that students followed more than 3,000 unique postsecondary pathways. Over two-thirds of the students (67 percent) graduated from high school and most either enrolled in postsecondary education or entered the workforce in the state immediately after graduation. Female students, White students, and urban students were more likely than male students, Alaska Native students, and rural students to enroll in college, respectively. However, students from each of these groups with similar academic and personal background characteristics had similar probabilities of enrolling directly after high school. In addition, students who earned a postsecondary degree tended to have higher early-career employment rates and wages than students who did not earn a degree. The findings provide evidence to inform policy and practice related to academic readiness and closing the gap in postsecondary enrollment rates between Alaska Native students and their White peers.