The purpose for this study was to determine what is the relationship between the degree of trust that the principals of middle schools and high schools invest in each other and the comprehensiveness of their eighth-to-ninth grade transition programs. Data were gathered through the administration of a three-part survey designed to collect information about (1) transition practices that directly involve principals, (2) transition practices that involve members of the school community other than principals, and (3) a principal-to-principal trust inventory. The anonymous survey was completed by 30 middle-school principals and 30 high-school principals from 64 school systems in Connecticut. These school districts shared a structure of having one middle school and one high school. Analysis of this survey led to the conclusion that there is a basic association between principal-to-principal trust and the comprehensiveness of transition planning and implementation; where there is a high degree of trust there is a corresponding greater comprehensiveness in transition activity. Conversely, where there is a lower degree of trust, there is also less comprehensive eighth-to-ninth grade transition program. [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/en-US/products/dissertations/individuals.shtml.]