Background: Despite recommendations for high-income countries to partner with low-income and middle-income countries to expand surgical access, little is known about the barriers that are faced by international surgeons (ISs) who participate in short-term clinical observerships in North America and the barriers that are encountered by their North American (NA) hosts. Methods: Surveys were distributed to ISs who participated in a pediatric orthopaedic observership in North America in 2009 to 2019 and their NA hosts to assess the perceived barriers that are faced by both partners and identify possible opportunities for improvement. Results: Responses were received from 181 ISs and 46 NA hosts. The ISs reported facing a variety of barriers prior to, during, and after completion of their NA observerships, including financial burden, language and cultural barriers, and challenges with local accommodations and transportation. Only 49% of ISs reported that their NA hosts had sought feedback from them. Barriers noted by the NA hosts included financial burden, logistical challenges with hosting, language barriers, and lack of support from their co-faculty/staff. At least 43% of NA hosts reported that their observership program was unfunded. Based on the survey responses, potential areas that may enhance the observership experience include funding support, creating a centralized data bank of pediatric subspecialty opportunities that are available at each sponsoring institution, a pre-visit orientation for the visiting surgeon, improving inclusivity by addressing language and cultural barriers, improving access to observing surgical procedures, obtaining post-visit feedback, and creating a virtual community of international visitors and NA hosts for an ongoing exchange of ideas and resources. Conclusions: The ISs who participated in a pediatric orthopaedic clinical observership and their NA hosts identified limited funding as a major barrier. There are several opportunities for enhancing this unique learning experience and exploring the role of contextual remote learning for all participants. Additional studies are needed to investigate the value of clinical observerships for ISs, including the downstream impact of such opportunities on capacity-building, bidirectional learning, and improving patient care.