As the last U.S. Census indicates, the Latina/o population is growing at an unprecedented pace: In 2010, 16% of the 309 million people living in this country were of Latino origin (U.S. Census Bureau, 2011). Many of these Latinas/os thrive, but others do not; they struggle to continue their lives and education in U.S. high schools and colleges (Suárez-Orozco, Yoshikawa, Teranishi, & Suárez-Orozco, 2011). Latinas/os are underrepresented at selective 4-year colleges and overrepresented at broad access community colleges and for-profit colleges (Carnevale & Rose, 2004). Further compounding the college selectivity dilemma are gender disparities in educational attainment, with Latinas enrolling in and completing college at higher rates than Latinos (Nuñez & Kim, 2012; Zarate & Burciaga, 2010). A third issue includes immigrant generation status attainment, as recent immigrants tend to have higher educational aspirations and success than their parents and Latinas/ os who have resided in the U.S. for longer periods (Conchas, Oseguera, & Vigil, 2012). What is missing from the college-going literature is how generational status may operate differently between Latinas and Latinos as well as how it may shape their college destinations. This chapter contributes to the gender gap discussion by examining the relationship between generational status, secondary school experiences, and postsecondary institutional destinations as one possible explanation of this gap. Our work addresses the following questions: (1) What role does generational status play in the postsecondary enrollment of Latina/o students? and (2) What is the strength and direction of secondary school conditions on postsecondary destinations of Latina/o students?