A key aim of Xu and Connelly’s (2013–2020) Canada–China Reciprocal Learning in Teacher Education and School Education Partnership Grant Project was to provide opportunities to appreciate different teaching practices and gain insights and reflections from cross-cultural collaborative educational endeavors. The Sister School Network, a component of this Canada–China Partnership, was established to build partnerships for mutual understanding and shared expertise in school education between China and Canada, through online communication (e.g., monthly Skype meetings) and face-to-face interactions (e.g., onsite visits). Activities included the sharing of students’ activities, guest teaching, collaborative lesson planning and co-teaching, video conferencing, and mutual onsite visits. Based on the authors’ observations and four graduate research assistants’ reflections on how teachers and students involved in the project communicated and collaborated over time, this chapter presents the challenges experienced in these collaborative activities, particularly related to the online conferences, and the strategies employed to overcome them. These challenges included technical difficulties, language barriers, time differences, and varying school calendars. Drawing on our findings, we offer considerations that we hope will not only enhance the reciprocal learning experience for students, teachers, and school administrators in the Sister School Network, but also inform researchers involved in similar projects with international partners.