My experience on a short term medical mission trip to Guatemala in 2010 left me with an uneasiness. In the face of the experience itself, much post-trip discourse has been centered largely on its value as social capital. The goal of my research is to begin to unravel the complex emotions that take place both at the site of contact in the third-world host country and after returning home. In the face of the ubiquity of short term mission trips, their increasing necessity for professional and educational development, and the vast amount of development literature, this emotional ambiguity is left out. I plan to unpack and illuminate this internal conflict as a way to understand the dual nature of its effects. As an overall objective, I hope that this project invites further discussion about short term volunteer programs and their complexities. Additionally, my research questions ask what evidence of this duality in their own experiences there might be in personal accounts of returnees. Additionally, I plan to address the source, context, and representation of this ambiguity, if it does in fact exist for others, as well. My methods consist of revisiting my experience through an autoethnography and collecting data from the trip. I also include personal narratives from several returned volunteers willing to share their experiences, as well as reviewing much of the academic literature about short term trips. I plan to present emergent broad themes and possible significance for others preparing to go on a short term volunteer trip. These themes include mixed feelings about the trip in the form of a duality, the manner in which relationships formed in the contact zone might affect personal beliefs about the work being done on the trip, and the ambiguity of short term mission trips in terms of their helpfulness or harm.