Assessment of teacher competence follows current educational trends in rubrics, standards, and high-stakes testing. Simultaneously, the traditional preservice education classroom is expanding into cyberspace; many teacher preparation programs are being offered through distance learning. As preservice education students complete required courses and classroom apprenticeships, they gain confidence and competence as future teachers; however, their new professional abilities must be measured objectively, which is especially challenging in on-line environments. Amid a growing reliance on standardized test scores, the capstone experience continues to grow in popularity. However, future teachers need to know more than educational theories and classroom practices once they leave the ivy-covered walls of their colleges and universities; they need professional touchstones. This article discusses a special educational mentoring program called the Teacher Opportunity Corps (TOC) at the Center for Urban Education at Pace University in New York City which emphasizes the role of preparative assessment as both a capstone and a touchstone. Reflections on the TOC preparative assessment model are presented.