Writing is a challenge to teach and difficult to assess. However, in this era of accountability, college-level writing must be assessed. The problem addressed in this case study was whether the writing ability of community college students could be authentically assessed. The purpose of this study was to seek to understand the nature of reflection in writing assessment. The experiences of first-year composition instructors, first-year composition students, and trained portfolio readers who participated in a new, holistically-scored portfolio course evaluation program at an urban, Midwestern community college were explored. The assessment required first-year composition students to submit a reflective letter that used the contents of their Composition I portfolio as evidence for an argument that the student had either met or not met the five goals of the course. There were two sources of data for this qualitative case study: the reflective letters, and the semi-structured interviews of the participants. The overarching research question for this inquiry was "what role does reflection play in the teaching, learning, and evaluation of writing?" Contained within that question are the three stakeholders who were involved in the writing assessment: the instructors, the students, and the readers. Although the secondary questions sought information from the stakeholders on how they described their understanding of reflection in light of their role in the program, the three implied questions in this study were: (a) can reflection be taught, (b) can students reflect, and (c) can reflection be recognized? The findings indicated that students can be taught how to reflect on their writing and that students can, and do, reflect. In addition, the researcher found that holistically-trained readers could distinguish between surface reflection and deep reflection in the students' reflective letters. A surprising finding was that the readers found the reading session helpful to them as instructors since it afforded them the opportunity to think reflectively about their own teaching. The researcher suggests ideas for future research and outlines implications for the three distinct stakeholders who could benefit from the findings in this study: composition students, writing instructors, and college administrators.