Bridging the Gap: Online Assessments presents a method of aligning secondary and postsecondary teaching of the higher verbal skills such as writing and critical thinking. Because the skills are verbal rather than quantitative and require subjective judgments, they are more difficult to assess accurately and consistently. Quality assessments require extended dialog and learning to develop a thorough understanding of the criteria and how to recognize them in context. Without a deep level of understanding, it is impossible for high school teachers to know whether their students is are adequately prepared for college. This is made possible by technology, which allows faculty to work on their own schedules, from home or anywhere they have high-speed Internet access. This initial research shows promise for a method of assessing very complex, detailed, extended student work that encompasses all the learning outcomes faculty value, while remaining flexible, convenient, and quite cost-effective. Teachers in the study not only achieved very high rates of inter-rater reliability (around 0.90), but also displayed deeper insight into their students'' learning and their own roles as teachers.