Small grants, engaging an army of trusted community messengers, ubiquitous marketing, and robust monitoring will be critical to enrolling the estimated 130,000 newly eligible CT Medicaid members in January 2014, according to a report by the CT Health Policy Project. Best opportunities for outreach include providers, current HUSKY members, faith-based communities, connecting with employers and other state programs, targeting life transitions, improving application and enrollment processes, and thanking outreach partners. It will require strong, concerted efforts to overcome the program’s stigma and other barriers to enrollment. The report draws on the experience of community organizers, consumer advocates who worked on HUSKY outreach, providers that care for CT’s uninsured patients, and lessons from other states. While aimed at Medicaid, many of the report’s findings also apply to the new CT Health Insurance Exchange.