Medical errors are the third leading cause of death in the United States, responsible for over a quarter million deaths per year, and clinical decision support (CDS) is intended, in part, to prevent many of these medical errors. As such, healthcare organizations (HCOs) are required and incentivized by regulatory bodies and patient advocacy groups to use CDS—but it often fails to deliver on its promise to improve patient safety. Further, the advisories provided by CDS systems are often not relevant to clinical work, leading clinicians to habitually bypass CDS alerts. This habitual bypassing is known as alert fatigue, which undermines the potential of CDS to improve the safety of the US healthcare system, and which may contribute to health IT-related burnout, a significant source of distress for clinicians. My dissertation research focuses on developing a better understanding of how well-intended regulations lead to unintended consequences, such as alert fatigue, which undermine efforts to improve patient safety. This better understanding will open the possibility of more meaningful and practical regulatory landscape that effectively protects patients without unduly interfering in clinical work.