Digital technology has been found useful in bridging the gap between school and work placements. In earlier studies we have interviewed vocational teachers with creative ideas on addressing this issue, but they encountered obstacles and could not always proceed as they wanted. The aim of this study is to provide a deeper understanding of the obstacles encountered by Swedish vocational teachers when using digital technology to bridge the gap between school and work placements. The study is based on a theoretical understanding of "teacher agency," and also presents a hierarchical model developed from our research. Ten in-depth interviews were conducted with five purposively selected vocational teachers. The teachers provided detailed examples of a range of problems stemming from structural, cultural and material aspects, and how these problems forced them to take steps backwards when trying to develop their teaching practices.