Green infrastructure 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). Regardless, overdesign may compromise plants’ access to water in systems where soil pits are embedded in infiltration beds. It could raise the storm size required for water to reach soil pits, reducing water availability between storms, which could ultimately induce plant physiological stress. This study investigated the hydrological dynamics and water relations of a tree trench system suspected to have been overbuilt and identified factors contributing to, compounding, and mitigating the risk of plant stress. Results provided strong evidence that the abovementioned processes played out. 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 the soil pit 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 either being largely confined to the soil pits or reaching a deeper water source. Implications of these results for green infrastructure design are considered.