This research paper discusses the accomplishments, issues, and challenges experienced by Open University of Sri Lanka (OUSL) academics when offering the first cross-border professional development online course to train online tutors and mentors. The course was delivered exclusively online and facilitated by OUSL academics and e-mentors from the USA. The course was comprised of 30 participants: 9 from Pakistan, 10 from Mauritius and 11 from Sri Lanka. This qualitative study is based on reflections of both faculty and participants. Data were collected using reflections and informal anecdotal records of the three OUSL academics and self-reflection instruments (pre, mid and final) administered to participants, and reflective journal entries made by participants. Participants' views were triangulated with the reflections of the OUSL academics to validate the results. While there were many accomplishments in the design and delivery of the course, the findings revealed that there were many challenges in implementing the course: pedagogical, organizational and technological aspects in particular. The paper provides recommendations to address such challenges when offering cross-border online courses in the future.