This chapter reports the challenges that both the students and the teachers experienced in a telecollaborative project between a Japanese university and an American university. In this semester-long project, the students in groups of three to five from both universities worked collectively mainly asynchronously and in occasional synchronous sessions. The project was originally designed in 2017 with the expectation of incorporating 'collaborative tasks' (O'Dowd & Ware, 2009), then redesigned in 2018. To examine how the students in both years perceived their collaborations and effectiveness, the results from online surveys from both years were compared. Furthermore, two groups from 2018, which experienced difficulties, were examined to reveal the causes of the problems. These results indicate that rather complicated tasks raised more logistical challenges than linguistic challenges. It became clear that the students experienced various challenges, which include scheduling synchronous sessions, unaligned visions on the final products, and lacking consideration for non-native speakers in synchronous sessions. These challenges in 'collaborative tasks' suggest that the success of a project is heavily dependent on the simplicity of the project design, sharing the same understanding at the beginning of the project, as well as the linguistic consideration to their group members. [For the complete volume, "Virtual Exchange in the Asia Pacific: Research and Practice," see ED610332.]