Although early field experiences are touted as vital for providing a hands-on preview of how teaching unfolds in the classroom, these essential components of teacher preparation programs have consistently fallen short of the desired outcomes. In the spirit of Dewey, candidates need substantive experiences that transform their theoretical learning into pedagogical knowledge. Likewise, Darling-Hammond (2006a) asserted that these experiences are strengthened when a collective team embarks on a mutual commitment, comprised of the candidate, university faculty, and talented teachers from cooperating schools. This article describes a project that sought to create technology-mediated early field experiences that maximized candidate learning in online content methods courses. The Windows into Teaching and Learning (WiTL) project was conceived and actualized by researchers in a large, urban university in the southeastern region of the United States. The initial objective of the project was to explore a means by which technology might facilitate meaningful field experiences for candidates enrolled in distance education classes. Several other potential outcomes arose from the project, allowing researchers to expand the initial scope to encompass potential benefits for all university teacher candidates conducting early field experiences as a part of their path to licensure. (Contains 3 online resources.)