For patients with venous thromboembolism (VTE), prediction of bleeding is relevant throughout the course of treatment, although the means and goal of this prediction differ between the subsequent stages of treatment: treatment initiation, hospital discharge, 3-month follow-up, and long-term follow-up. Even in the absence of fully established risk prediction schemes and outcome studies using a prediction scheme for treatment decisions, the present evidence supports screening for and targeting of modifiable risk factors for major bleeding, as well as the application of decision rules to identify patients at low risk of bleeding complications, in whom long-term anticoagulant treatment is likely safe. Moving forward, prediction tools need to be incorporated in well-designed randomized controlled trials aiming to establish optimal treatment duration in patients at high risk of recurrent VTE. Moreover, the benefit of their longitudinal assessment rather than application as stand-alone baseline assessments should be studied, because changes in bleeding risk over time likely constitute the best predictor of major bleeding. We provide the state-of-the-art of assessing and managing bleeding risk in patients with acute VTE and highlight a practical approach for daily practice illustrated by 2 case scenarios. Display omitted