Information Technology (IT) surrounds us every day. IT products and services from smart phones and search engines to online banking and stock trading have been transformative. However, IT has made only modest and less than disruptive inroads into healthcare. This article explores the economic and technological relationships between healthcare and healthcare information technologies (HIT), asks (leveraging the work of Clayton Christensen) whether current conceptions of HIT are disruptive or merely sustaining, and canvasses various explanations for HIT’s failure to disrupt healthcare. The conclusion is that contemporary HIT is only a sustaining rather than disruptive technology. Notwithstanding that we live in a world of disruption, healthcare is more akin to the stubborn television domain, where similarly complex relationships and market concentrations have impeded the forces of disruption. There are three potential exceptions to this pessimistic conclusion. First, because advanced HIT is not a good fit for episodic healthcare delivery, we may be experiencing a holding pattern while healthcare rights itself with the introduction of process-centric care models. Second, the 2010 PCAST report was correct, the healthcare data model is broken. If Stage 3 of the MU subsidy program or some other initiative can fundamentally rethink interoperability (and we can fix the privacy issues) investment and innovation will migrate to data services built on top of shareable data. The final and potentially most interesting exception may be Mobile Medical Apps; products that are built on hugely disruptive platforms and championed by some of our most disruptive companies. Leveraging the growing computing power of smartphones and linkable biometric sensors, these apps hold the promise for “healthcare everywhere” and may be where the real disruption of healthcare will begin.