This correlational study examined factors that defined the experiences of high school students who navigated the postsecondary pipeline in pursuit of a postsecondary education. Data for this study were obtained from the 2002 Education Longitudinal Study conducted by the National Center for Education Statistics. The factors explored were related to student attitude and interest in school, absenteeism and behavior, academic engagement, and preparedness. These variables were studied alongside race, gender, and socioeconomic status. The potential moderating factor of first-generation student status was of key importance. Binary and multinomial logistic regression analyses were conducted to understand which variables are significant predictors of postsecondary pipeline outcomes. This study found several variables to be significant predictors. Moderation by first-generation student status was significant or near significant for several variables including (i) cutting or skipping school, (ii) absenteeism, (iii) attitude towards grades, and (iv) the frequency that a student attended class with no homework, with first-generation students being at a disadvantage as the frequency of each of these undesirable variables increased, controlling for a vector of demographic variables. Overall, first-generation students had lower probability of success in terms of completing the postsecondary education pipeline compared to their counterparts. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]