Infiltration-induced landslides threaten transportation infrastructure around the world, and impose both direct costs through repair and remediation work and indirect costs through lost economic activity. Therefore, finding the most cost-effective techniques to mitigate slope failures that can impact critical infrastructure links is desirable. The Straight Creek landslide, which affects a segment of Interstate 70 in Summit County, Colorado (USA), has experienced seasonal failure driven by rapid springtime snowmelt infiltration since the early 1970s, allowing changes in its stability to be studied. Past studies have established that seasonal failure is driven by pore-water pressure increase caused by the rapid infiltration of snowmelt and the hydraulic conductivity contrast between upper slope materials and the highway embankment. Two remediation designs have been applied to the site, including lightweight caissons beneath the highway surface in 2011 and 2012, and horizontal drains near the slide toe in 2012. The effects of the lightweight caissons and horizontal drains, as well as an alternative drain design that would extend into the hillslope above the highway embankment, are evaluated within a rigorous hydro-mechanical simulation framework along with a method to generate a field of local factor of safety. Model results show that the effect of the lightweight caissons on the factor of safety is no more than 1% during times of critical instability, as they do not affect the seasonal changes in hydrology that cause destabilizing decreases in effective stress along the failure surface. Horizontal drains are intended to reduce pore-water pressures, but the location of existing drains limit their efficacy due to the low hydraulic conductivity of subsurface materials underneath the highway. Model results indicate that these drains are only partially responsible for a reduction in movement rate since their installation, which is also due to lower annual cumulative snowmelt infiltration levels since 2012. Results also show that an alternative drain design could result in increased stability during critical periods by intercepting downslope subsurface flow before it arrives at the hydraulic conductivity contrast at the embankment.