Studies show that there are far greater numbers of individuals certified to be educational administrators than of positions requiring such certification. Yet concerns regarding shortages abound, in part because of widespread perceptions of a lack of interest by teachers and administrative certificate holders in administrative work. This study takes a close look at the pipeline into educational administration to determine whether decisions on the supply side, demand side, or both are responsible for the movement (or lack thereof) of individuals into administration. Research Design: This study employs survey and administrative data from 2002 to 2006 to track a sample of administrative certificate earners in Illinois through the pipeline into administrative positions. Using application and job offer information, the authors identify who applied for administrative jobs, received job offers, and accepted administrative positions and assess using logistic regression models factors associated with the decisions of prospective employees and employers in this labor market. Findings: Although a majority of respondents attempted to obtain administrative positions within 2 years of completing administrative certification, a substantially smaller percentage actually became administrators. This study reveals that approximately 30% of eligible respondents are lost at each stage-application, job offer, and job acceptance. Conclusions: Multiple factors contribute to the loss of Article DeAngelis and Kawakyu O'Connor 469 prospective administrators from the pipeline into educational administration. The findings suggest that more job-specific training opportunities and greater support and encouragement throughout the transition process would stem some of the loss of prospective administrators.