Rough River Dam is a high hazard flood risk management embankment dam, owned and operated by the US Army Corps of Engineers (USACE), located in west-central Kentucky. The valley overburden soils were left in place with no positive seepage cutoff. The 1950s-era dam designers called for the installation of upstream and downstream filter blankets and sand wells to overcome high pore pressure build-up in the fine-grained soil foundation while constructing the embankment. Long-term poor performance associated with the features resulted in past remediations and a planned future major rehabilitation to install a cutoff wall. This paper will provided a historical retrospective for the design, construction, and performance of upstream drainage features at Rough River Dam along with comparisons to other known dams with similar upstream drainage features. This retrospective shows that dams with upstream filters and/or drains, without a positive foundation cutoff or adequate filters, should be flagged by dam owners for increased monitoring and evaluation.