The purpose of this study was to collect and analyze demographic characteristics and job related difficulties experienced by field instructors in outdoor behavioral healthcare programs which utilized wilderness therapy as well as other treatment modalities. Three state-licensed outdoor behavioral healthcare programs in the United States provided a sample of 129 field instructors who completed the survey. Results confirmed a high turnover rate of instructors and high challenges experienced with non-work related issues, particularly in sustaining romantic personal relationships. Factor analysis identified three constructs related to difficulty levels experienced on the job: a) time and schedule constraint; b) emotional anxiety and stress-related issues; and, c) physical and mental challenges. Results of this study are of value to field instructors and outdoor behavioral healthcare program administrators to better understand the challenges faced by this group of professionals. Recommendations are presented that suggest ways that the physical and mental health of field instructors can be supported.