Venous thromboembolism (VTE) has serious consequences for patients with cancer, including mortality. VTE is preventable with appropriate thromboprophylaxis, but prior public health efforts have focused on prophylaxis in the inpatient setting. However, most VTE events in malignancy currently occur in outpatients. Several recent clinical trials have addressed thromboprophylaxis in the ambulatory setting. Their findings suggest potential benefit, but with significant variation in underlying risk. A risk-adapted approach that incorporates risk of thrombosis, risk of bleeding, and patient preference can target high-risk patients and also allow low-risk patients to avoid prophylaxis. Risk assessment is therefore key to patient selection for outpatient prophylaxis. This article focuses on results of recent trials and updates from major guideline panels, with the intent of providing guidance to clinical providers.