This study explores the challenges of data compliance in the U.S. healthcare system, focusing on the implementation of the Health Insurance Portability and Accountability Act (HIPAA) and the Health Information Technology for Economic and Clinical Health (HITECH) Act. The aim is to identify gaps in the regulatory frameworks and propose solutions to enhance compliance in the context of rapid technological advancements. A qualitative methodology was employed, incorporating case studies, industry reports, and academic literature to analyze vulnerabilities in healthcare data security and evaluate the effectiveness of existing regulations. Findings indicate that although HIPAA and HITECH have established a strong foundation for protecting Personal Health Information (PHI), they increasingly fail to address modern challenges such as cloud computing, internet of things (IoT) integration, and cybersecurity threats. Systemic barriers, including resource constraints, inconsistent standards, and insufficient technical expertise, further increase the risks of noncompliance. Despite federal initiatives like the HITRUST framework providing enhanced guidance, these efforts require greater adaptability to meet the demands of evolving healthcare IT infrastructures. The study concludes that advancing data compliance necessitates a multifaceted approach, including revising regulatory frameworks, fostering interdisciplinary collaboration, and developing a skilled workforce proficient in healthcare cybersecurity. The researchers argue that these measures will strengthen PHI protection, foster innovation in healthcare delivery, and ensure a secure and compliant healthcare ecosystem.