We hypothesized that psychiatrists with high dual-agency potential (military and health maintenance organization [HMO] psychiatrists) were more likely than non-HMO civilian psychiatrists to engage in dual relationships, report pressures to do so, participate in other general boundary-crossing activities, and report associated counter-therapeutic outcomes (boundary violations). Ninety military and 191 demographically matched civilian psychiatrists reported the number of boundary-crossing activities (including dual relationships) and associated counter-therapeutic outcomes in the preceding year with adult patients. Military and HMO psychiatrists reported greater external pressures than non-HMO civilian psychiatrists to engage in dual relationships; however, all three groups were similar in their reported numbers of dual relationships. The reported boundary-crossing activities and dual relationships studied here are not necessarily associated with reported boundary violations. The relative risk of a particular boundary crossing associating with harm to a patient likely depends on the therapeutic context and should be determined on a case-by-case basis.