The large number of underprepared students entering the nation's two-and four-year colleges and universities has created what Levin and Calcagno (2008) consider a "remediation crisis" (p.181). Despite the recent attainment of high school diplomas, many incoming students are academically unprepared for college-level coursework in reading, writing, and mathematics (Levin & Calcagno, 2008). The disconnect between high school competencies and college readiness poses a serious threat not only to President Obama's ambitious goal of having the highest proportion of college graduates in the world by 2020 (President Obama, Address to Joint Session of Congress, Feb. 24, 2009), but most importantly to the academic and career goals of today's youth. As Calcagno, Crosta, Bailey and Jenkins (2007) have noted, students who enter college through remedial pathways are less likely to graduate. The misalignment between K-12 and postsecondary expectations is a cause for serious concern, and educators must work together to bridge this ever-widening gap. Attempts to create a seamless K-16 system have been stymied by the severe lack of information that K-12 and postsecondary educators as well as prospective college students have regarding each other's expectations and goals. This article explores the effects of misalignment on assessment, current state initiatives, and using collaboration and communication for better alignment. It concludes that colleges and universities may have varied perceptions of students' college-readiness based on the selectivity of the institution. Creating a seamless K-16 pathway is undoubtedly challenging; however, it seeks to improve student outcomes by increasing access and enhancing academic support. President Obama has set an ambitious goal that will require cooperation and collaboration from educational institutions at all levels as it depends greatly on the ability of P-16 institutions to retain and strengthen students.