This case study describes the experiences of two preservice teachers as they attempt to integrate the use of technology into instruction during their field placement experiences. What factors influence the decisions they made about how and when to teach with technology? How do these factors enable or disable their abilities to gain experience teaching with technology during their field placement experiences? This case is part of a larger study of six preservice teachers, engaged in a program designed to prepare new teachers to teach with technology. This program received $1,3000,000 from the U.S. Department of Education, which was 50% of the total cost. The remaining funding came from a university, school, and business match. Data collected from surveys, interviews, and written reflections was examined to help identify enabling and disabling factors, and gain an understanding of how those factors influence practice.