As many developed nations are experiencing rapidly aging populations and a projected shortage of medical professionals, the use of semi and fully autonomous digital technology in the field of medicine offers the potential to improve healthcare within the essential parameters of quality, access and cost. Digital medical technology can take many forms including: wearable sensors and mobile phone applications that track the health of individuals; hand-held devices that augment the diagnostic and treatment capabilities of medical providers; and autonomous smart machines that can process massive amounts of data and rapidly recognize patterns that correlate with disease or successful treatment options. However, in many jurisdictions, healthcare laws and regulations have not evolved to address the significant legal issues that digital medical technologies present. In particular, issues related to liability, privacy and professional autonomy pose serious regulatory challenges. Failing to account for these legal issues could either form a barrier to fully adopting this technology or lead to unaddressed harms. Medical liability stemming from failures or misapplication of these new technologies presents a large risk for individual or small group providers to assume. Thus, enterprise liability or sovereign liability with a no-fault compensation scheme could address this concern by spreading out the malpractice liability risk while ensuring compensation for injured patients. Maintaining the legitimate level of protection for sensitive medical data represents a daunting challenge that requires regulations on individuals, organizations and the underlying technology. In addition to factoring in political and cultural norms within privacy regulations, there is a tension between strong protections of personal medical information and enabling analytic breakthroughs that benefit from open access to such data. Lastly, professional autonomy portends to be a complex issue, particularly depending upon one’s particular training and skill set. Medical providers that primarily rely on pattern-recognition skills will feel the greatest competitive threat from digital technology. In contrast, medical providers with skills that do not lend themselves to automation may experience significant augmentation of their abilities from these new technologies.