Self-monitoring has been shown to improve academic performance across a variety of subjects. This study investigated the effectiveness of a self-monitoring checklist on the writing skills of five students in an urban Midwestern elementary school. At the end of 10 min in-class writing assignments, participants counted the total number of words written and answered five questions related to writing mechanics. Using a multiple baseline across subjects design, baseline levels of total words written (TWW), words spelled correctly (WSC), and correct minus incorrect writing sequences (CIWS) on weekly curriculum based measures were compared to intervention levels for each student, in addition to follow-up maintenance assessments. Results showed moderately positive effects on CIWS for Student 1 and mildly positive effects for Students 2 and 3. No effects were seen for Students 4 and 5, however, there were only two intervention points for Student 5, making it difficult to draw strong conclusions. Maintenance data demonstrated continued positive effects for Students 1 and 4. Acceptability of the self-monitoring procedures was demonstrated through positive results on student questionnaires and informal verbal report from the teacher.