Social media and the ways in which educational leaders choose to utilize it their schools is at the forefront of professional development throughout numerous districts across Long Island and nationwide. While many districts have incorporated various models of social media such as Facebook, Twitter, and Instagram into their standard communication practice, many more are hesitant to venture into this type of contact with the school community for a variety of reasons. Historically, school leaders relied on letters to parents sent home either by US mail or in their child's backpacks to convey times and locations of meetings and to send important messages (including, but not limited to school practice and policies and dates for upcoming events). In the past ten years, school leaders have begun using websites and email to send important messages out to the school community. This study involved an in-depth examination of the literature surrounding the importance of the home-school connection and how school leaders are using the social media platform of Twitter in an effort to strengthen this relationship. Further discussion included how the ideals of branding a business are beginning to emerge in the school setting in order for the leader to have the ability to tell their own school's story rather then having others tell it for them. Three school leaders currently engaged in the daily use of Twitter were interviewed, as well parents and teachers in the school community. Pertinent documents were reviewed, including school district policy on the use of social media and an analysis of the "tweets" sent out by the school leader. The findings of this study revealed how school leaders use Twitter to engage the school community and "brand" their school by having the ability to control the information that is shared with the public. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]