The launch of HealthCare.gov, the website of the Affordable Care Act (AKA Obamacare), was a major public relations disaster for the Obama administration. This case examines some of the factors that contributed to the failure of the launch and then details how Optum, an information technology service provider, considered the opportunity provided by the failure. The case provides examples of both good and bad IT management processes and poses questions for discussion related to the evaluation of risk associated with high profile projects.