We have developed groundwater flow models to explore the possible relationship between wastewater injection and the 12 November 2014 M_w 4.8 Milan, Kansas earthquake. We calculate pore pressure increases in the uppermost crust using a suite of models in which hydraulic properties of the Arbuckle Formation and the Milan earthquake fault zone, the Milan earthquake hypocenter depth, and fault zone geometry are varied. Given pre‐earthquake injection volumes and reasonable hydrogeologic properties, significantly increasing pore pressure at the Milan hypocenter requires that most flow occur through a conductive channel (i.e., the lower Arbuckle and the fault zone) rather than a conductive 3‐D volume. For a range of reasonable lower Arbuckle and fault zone hydraulic parameters, the modeled pore pressure increase at the Milan hypocenter exceeds a minimum triggering threshold of 0.01 MPa at the time of the earthquake. Critical factors include injection into the base of the Arbuckle Formation and proximity of the injection point to a narrow fault damage zone or conductive fracture in the pre‐Cambrian basement with a hydraulic diffusivity of about 3–30 m²/s. The maximum pore pressure increase we obtain at the Milan hypocenter before the earthquake is 0.06 MPa. This suggests that the Milan earthquake occurred on a fault segment that was critically stressed prior to significant wastewater injection in the area. Given continued wastewater injection into the upper Arbuckle in the Milan region, assessment of the middle Arbuckle as a hydraulic barrier remains an important research priority.