The implementation of the United States Environmental Protection Agency's National Pollutant Discharge Elimination System-Municipal Separate Storm Sewer Systems, or NPDES-MS4 permits, represents a real challenge to cities around the United States of America and its territories. Such is the case in the Commonwealth of Puerto Rico, which is undergoing a serious financial crisis in most of its municipalities due to industrial, economic, and tax-related transformations. This crisis, along with rigorous environmental laws and regulations at the federal level, require municipal governments to prioritize where to invest their limited funding for the improvement of their jurisdiction's environmental quality. In addition, the intrinsic natural, economic and social characteristics of this US territory in the Caribbean make the enforcement of the NPDES-MS4 program extremely challenging. The allocation of both human and economic resources to comply with the regulations requires new approaches and strategies, as is integrating technology and web-based tools for a more efficient use of time as well as financial accountability. The use of technological devices and programs is critical to advance in the implementation of compliance programs. Easily operated software or equipment proves to be effective in helping municipalities to strengthen their local enforcement ordinances, which are a key element for the success of the NPDES-MS4. Since 2015, we have identified and categorized over 1,000 illegal discharges in twelve municipalities. Integrating modern tools, such as the web-based permit managers, has provided municipalities with a much-needed capability to address efficiently some of the environmental issues we face now a day. The flexibility offered by the new technology has proven very effective helping municipalities to establish a robust data management strategy aimed to implement their environmental permits while saving thousands of dollars on inspection costs.