Environmental regulations can only be effective if they are adhered to, but the motivations for regulatory compliance are not always clear. We assessed vessel operator compliance with a December 2008 regulation aimed at reducing collisions with the endangered North Atlantic right whale that requires vessels 65 feet or greater in length to travel at speeds of 10 knots or less at prescribed times and locations along the U.S. eastern seaboard. Extensive outreach efforts were undertaken to notify affected entities both before and after the regulation went into effect. Vessel speeds of 201,862 trips made between November 2008 and August 2013 by 8,009 individual vessels were quantified remotely, constituting a nearly complete census of transits made by the regulated population. Of these, 437 vessels (or their parent companies), some of whom had been observed exceeding the speed limit, were contacted through one of four non-punitive information programs. A fraction (n = 26 vessels/companies) received citations and fines. Despite the efforts to inform mariners, initial compliance was low (<5% of the trips were completely <10 knots) but improved in the latter part of the study. Each notification/enforcement program improved compliance to some degree and some may have influenced compliance across the entire regulated community. Citations/fines appeared to have the greatest influence on improving compliance in notified vessels/companies, followed in order of effectiveness by enforcement-office information letters, monthly summaries of vessel operations, and direct at-sea radio contact. Trips by cargo vessels exhibited the greatest change in behavior followed by tanker and passenger vessels. These results have application to other regulatory systems, especially where remote monitoring is feasible, and any setting where regulatory compliance is sought.