The objective of this study was to ascertain the reasons why a specific urban Catholic high school was successful with a highly at-risk population of students. The school examined in this study was named Dylan High School. A common phrase discussed at this school when referencing student success was a phenomenon called the "Dylan Way." However, it was uncertain exactly what the "Dylan Way" was and what it entailed. Therefore, the proposed study examined the following question, "What is the Dylan Way and in what way, if any, do stakeholders connect the Dylan Way with student success?" To thoroughly answer this research question, five key sub-questions were examined: (1) How do school leaders define the "Dylan Way?" (2) How do teachers define the "Dylan Way?" (3) How do students define the "Dylan Way?" (4) How do parents/guardians define the "Dylan Way?" (5) In what way, if any, do stakeholders connect the "Dylan Way" and student success? This study utilized a qualitative research design with a positioned subjects approach within a single case study. Data was collected mainly by means of interviews, in a one-on-on format. These interviews addressed such things as existing school procedures, practices, and policies that impacted student success at Dylan. Document analysis complemented interviews of persons in this context and contributed to a richness of data collected and analyzed. Data derived from participants' or stakeholders' views of the "Dylan Way" and the aimed to make sense of and interpret the meanings others have about this phenomenon. The theory or pattern of meaning from the data focused on a particular community--Dylan High School--and the characteristics that led to successful student outcomes. By defining both the theory at work within the "Dylan Way" and success within this context, the findings reflected transferable lessons for increasing student success in other urban high school settings. [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.]