Clinical documentation in the pre-hospital setting is challenged by limited resources and fast-paced, high-acuity. Military and civilian medics are responsible for performing procedures and treatments to stabilize the patient, while transporting the injured to a trauma facility. Upon arrival, medics typically give a verbal report from memory or informal source of documentation such as a glove or piece of tape. The development of an automated documentation system would increase the accuracy and amount of information that is relayed to the receiving physicians. This paper discusses the 12-week deployment of an Automated Sensing Clinical Documentation (ASCD) system among the Nashville Fire Department EMS paramedics. The paper examines the data collection methods, operational challenges, and perceptions surrounding real-life deployment of the system. Our preliminary results suggest that the ASCD system is feasible for use in the pre-hospital setting, and it revealed several barriers and their solutions.