Today’s United States Coast Guard (USCG), which was formed by the merger of the US Revenue Cutter Service and the US Lifesaving Service, was founded in 1790. While the service and its assets have been modernized, many of the support facilities have been updated at a slower pace. Two USCG sites, Base Elizabeth City, North Carolina (NC) and the housing site for Station Valdez, Alaska (AK) are both examples of locations that have been in existence prior to the 1970’s and therefore both locations require upgrades to comply with today’s more stringent water quality standards. This paper provides two case studies where existing systems were not meeting current water quality standards. The first case study in Valdez, AK looks at a stormwater management system that was not in compliance with Environmental Protection Agency (EPA) regulations. The second case study in Elizabeth City, NC examines an on-site wastewater treatment system that is discharging volatile organic compounds and heavy metals in excess of the allowable EPA discharge limits. These two projects share common challenges due to infrastructural limitations, economic issues, and environmental regulations. To address the current on site challenges, this paper offers guidelines that can serve as a reference framework for future Coast Guard environmental projects.