This article describes and illustrates how we use the concepts of collaborative inquiry and transaction between organism and environment developed by Dewey to design and experiment video-enhanced learning environments in teacher education and professional development programs. Inquiries conducted on these video-enhanced learning environments are based on traces of filmed activity and experience of work. It aims to enable the participants to the inquiry to transform their teaching activity and develop professionally. The article explores the different transactions that participants can experience when confronted with the traces of their activity, the inter-objectification of their own activity during the inquiry, and spaces of new meanings that are created. Finally, it describes the principles, modalities and conditions of operationalization that structure such video-enhanced environments and the tensions that facilitators encounter during the program, given the open structure of the collaborative inquiry and the practical rationality it implies.