This article discusses the development and implementation of a technology-supported student teacher performance assessment that supports integration with a larger electronic assessment system. The authors spearheaded a multidisciplinary team to develop a comprehensive performance assessment based on the Pathwise framework. The team collaborated with a third party vendor to implement and field test these assessments supported with mobile technologies in the field. Twenty supervisors completed the field test using 10 iPAQ PDAs and 10 laptops. Eighteen participated in a posttest survey and eight in a focus group debriefing session. Supervisors were overwhelmingly positive about the experience, the value of the updated assessments, and the ongoing plans to support field observations with mobile technologies. However, issues related to training, support, and trust loom largely for successful adoption, diffusion, and successful use of technology-supported assessments.