Green infrastructure (GI) systems are often overdesigned. This may be a byproduct of static sizing (e.g., accounting for a design storm’s runoff volume but not exfiltration rates) or may be deliberate (e.g., buffering against performance loss through time). In tree trenches and other GI systems that require stormwater to accumulate in an infiltration bed before it contacts the planting medium, overdesign could reduce plant water availability significantly. This study investigated the hydrological dynamics and water relations of an overdesigned tree trench system and identified factors contributing to, compounding, and mitigating the risk of plant stress. Water in the infiltration bed reached soil pits only once in three years, with that event occurring during a hydrant release. Moreover, minimal water was retained in soil pits during the event due to the hydraulic properties of the soil media. Through a growing season, one of the two tree types frequently experienced water stress, while the other did so only rarely. These contrasting responses can likely be attributed to roots being largely confined to the soil pits vs. reaching a deeper water source, respectively. Results of this study demonstrate that, in systems where soil pits are embedded in infiltration beds, overdesign can raise the storm size required for water to reach the soil media, reducing plant water availability between storms, and ultimately inducing physiological stress.