This commentary explores the clinical conundrums arising when caring for patients with acute pulmonary embolism isolated to the subsegmental pulmonary arteries. We discuss ways to confirm the radiologic diagnosis, how to distinguish patients for whom anticoagulation is indicated from those who are eligible for structured surveillance without anticoagulation, what surveillance entails, and why ensuring continuity of care matters. We report a case from our own experience that illustrates these decision-making crossroads and highlights the importance of cross-disciplinary collaboration. Because the evidence in the literature is currently weak and indirect, we draw on expert opinion in US and European guidelines, a recent statement from a multidisciplinary consensus panel, and several ongoing well-designed clinical trials. This discussion will help clinicians better manage the spectrum of patients who present with isolated subsegmental embolism.