This article discusses the challenges faced when integrating new technologies into the classroom. Viewing the experiences of teaching a first year learning community through the lens of the principles of the Reflective Teaching Portfolio, the author looks to answer the question: "How should Technology relate to our Teaching Philosophy?" While a proponent of testing and integrating new technologies into the classroom, the author also recognizes that we learn more from our mistakes than from our successes and that if a tool does not fit with our Teaching Philosophy, then we should not use it. This article provides an honest assessment of recent experiences integrating online learning technologies into the classroom and makes suggestions on how to develop a successful approach.