Despite recent policy initiatives to ensure high school accountability through state-mandated testing, New Jersey high school graduates may not be prepared for the challenges of college-level writing because the state's high school assessment is not aligned with college-level expectations (Brown & Conley, 2007; Conley, 2003). An ever-growing library of reports acknowledge that many states in addition to New Jersey have not aligned their high school tests in writing with college expectations (Achieve, 2007; Silva, 2008); however, other surveys suggest there is alignment between high school writing curriculum and higher education admission tests (Le, 2002; Milewski, Johnsen, Glazer, & Kubota, 2005). This study, therefore, was designed to describe and understand alignment between writing skills needed for success on the high school assessment in comparison to the writing skills that will be demanded of students in college. This study used the judgments of a group of eight writing instructors to collect in-depth information on how the New Jersey High School Proficiency Assessment (HSPA) writing scoring rubric aligns with college-level standards for success, as defined in the Knowledge and Skills for University Success (KSUS). In addition, instructors also examined 20 sample HSPA writing responses and provided judgments about whether the essays demonstrated college readiness. Individual interviews were held with all eight participants, and their judgments were coded to further understand what characteristics of HSPA responses demonstrated college preparedness. From performing these analyses, this study's results corroborate with previous studies on the HSPA (Conley, 2003). The HSPA provides some indication of how students can organize writing in test situations, but the HSPA does not align as well with the type of critical thinking and reading-writing synthesis work that will be required at the college-level. These results suggest that policymakers should consider revisions to the HSPA writing test such that it would require students to demonstrate skills in using evidence to sustain cogent arguments. [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/en-US/products/dissertations/individuals.shtml.]