Teachers use situated knowledge to deal with the complex and diffuse educational contexts they operate in. To be able to take deliberated action, based on the situated knowledge, reflection is necessary during the teacher training. Video cases with common, real world situations are suitable for reflection because of their holistic and diffuse character. Reflection concerns learning experiences with increasing complexity: single-loop (reflecting on a current action), double-loop (reflecting to gain new insights) and triple-loop (reflecting in order to adjust individual identity) learning. The knowledge gained from loop learning is of a situated nature. The current article operationalizes situated knowledge as educational purposes and design patterns; educational purposes determine which course of action (design pattern), is the best option. Using this distinction, we investigate whether the reflection done by fourth-year teachers in training corresponds to what can be expected of a starting expert, namely, reflection on all three levels. The results indicate that three out of four teachers in training can be characterized as starting experts, based on their responses to a video case. They experience learning on all three loop levels, and these experiences contribute to a variety of educational purposes and design patterns. It is the teacher trainers' challenge to have their students reflects using video cases, so they can use loop-learning to build their situated knowledge. This knowledge will allow them to adequately respond to the complex and diffuse situations in their educational practice.