Purpose: Regulatory compliance is a vital part of governance, ensuring that programs across various sectors are implemented effectively and without errors. This study focuses on the Virginia Beach Housing & Neighborhood Preservation department, examining how it managed the CARES Act and HUD ARPA legislation, two significant federal regulations introduced during challenging times. The integration of these laws into existing local policies presented a range of difficulties, including conflicts, misinterpretations, and delays. This research analyzes those challenges and offers strategies to streamline compliance in future situations. Methodology: To better understand the regulatory hurdles, this study employed a thorough document analysis and compared housing sector compliance issues with those faced in healthcare. Both sectors deal with strict regulations, and non-compliance can have serious consequences. In healthcare, for instance, lapses in compliance can endanger patient safety, while in housing, they can lead to administrative inefficiencies and misuse of resources. By drawing this comparison, the study highlights the broader implications of effective compliance systems across different sectors. Findings: The findings show that regulatory compliance not only helps reduce errors but also enhances overall program performance. The challenges faced by the Virginia Beach Housing & Neighborhood Preservation department serve as an example of the obstacles organizations encounter when implementing new regulations. The solutions proposed in this study offer a clear path for improving compliance systems and reducing operational disruptions. Unique Contribution to Theory, Policy and Practice: Ultimately, this study emphasizes the importance of robust compliance frameworks in ensuring efficient program execution. It argues that proper management of compliance not only mitigates risks but also contributes to better outcomes across various sectors. By offering practical strategies for overcoming compliance challenges, this research adds valuable insights to the field and supports the ongoing development of effective regulatory practices that benefit both organizations and the communities they serve.