Cross-laminated timber (CLT) is revolutionizing the use of wood in the construction sector of North America as a solution for walls and diaphragms in mid-rise or even high-rise timber structures on account of its environmental advantages, high strength-to-weight ratio, fire-safety performance, and propensity for prefabrication. However, considering the hygroscopic nature of wood, moisture intrusion can affect material properties and, moreover, moisture increases the possibility of biological degradation, which can directly affect the durability of CLT structural members and their connections. The favorable seismic performance of connections in the CLT structural systems has been well researched in numerous studies. In addition, even though several research efforts have been conducted to understand the hygrothermal performance of CLT panels, knowledge of the CLT connections when subjected to moisture cycling is minimal. In this study, a CLT shear wall-to-diaphragm L-bracket connection is exposed to two high moisture exposure conditions - flood and simulated rain with increased humidity as well as different exposure durations to investigate the connection performance under the effects of moisture intrusion. Currently, there are four major species that are used for CLT, namely, Douglas-fir, Southern yellow pine, Norway spruce, and Spruce Pine Fir. All four species were incorporated into the study. A total of 264 cyclic tests were performed on wall-to-diaphragm L-bracket connection specimens to evaluate the connection performance in terms of strength, stiffness, and energy dissipation along with the development of two force-displacement engineering models. Results from both exposure studies suggest no significant degradation in connection performance after a moisture cycle of wetting and drying apart from a significant decrease in energy dissipation in flood exposure. However, the effects of multiple moisture cycling merit further study.