This qualitative study investigated teachers' perceptions of their own writing abilities and processes, the adequacy of their pre-service teacher preparation, and the efficacy of in-service, school system and school building-level support, and how each of these components affected the educator's aptitude to teach students in grade six through eight how to write effectively. The embedded multiple case study design examined one parochial school system located in suburban New York with middle school teachers as the different cases. A qualitative survey was the research method applied. Subsequently, individual interviews were conducted to acquire more specific information from teachers with different educational backgrounds, years of teaching experience, and from different school buildings within the school system. Both thematic and cross-case analyses were used to analyze the collected data, which ultimately led to a synthesis of overarching commonalities and trends. First, teacher preparation programs did not fully prepare the educators to effectively teach middle school writing. Additionally, the teachers' self-perceptions as writers became a factor in effectively teaching writing, and finally, teacher support is misguided and largely ineffective in the school system. To increase the confirmability of the study's findings, strategies that ensured the study was consistent, valid, and transferrable were implemented throughout the research process. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]