Being a “good” doctor nowadays involves more than having virtues and capacities conducive to the content of encounters between physicians and patients. Physicians can and must be able to act on the surrounding conditions of the doctor-patient encounter, in order to keep external interests at bay. Hence, the patient-related virtues, such as compassion, prudence, temperance and the like might not constitute sufficient cause for “good” doctoring. Resistance against the invasion of external interests requires another set of capacities. In this compilation thesis, one such capacity is explored: cunning. While certainly not part of the repertoire of skills in relation to the patient, cunning intelligence is an indispensable “virtue” of good doctoring insofar as doctors must cleverly navigate institutions that block off paths toward the ultimate ends of healthcare. The role of cunning is examined through a particular case, namely, the struggle over social insurance, especially sickness benefits (“sjukpenning”), and the complex relationship between physician, patient and the Swedish Social Insurance Agency (“Försäkringskassan”). In these times of increased austerity, physicians have honed skills, retaining thereby good medical practice, and by extension also maintaining the integrity of the patient-related virtues of medicine. In the empirical material, techniques were identified, particularly with respect to the way in which the sickness certificate is written to ensure approval by the SSIA. Based on these findings, the ambiguities, contradictions and possibilities inherent in the cunning resistance of physicians are analyzed and problematized. Despite its many issues, what doctors do when issuing sickness certificates in this particular way, is certainly motivated and carried out by more than mere ignorance. Cunning intelligence is not merely a defective form of prudence (phronesis), nor is it simply an instance of instrumental reason (techne), but rather an ability that occupies a distinct place among the intellectual abilities generally ascribed to professionals. Finally, I explore if the use of these capacities indicates a change in the doctor-patient relationship. I argue that both doctor and patient are conditioned by an equality in powerlessness—the hallmark of “the age of bureaucratic parsimony”, which can be appropriately described in terms of solidarity between comrades.