Intracranial haemorrhage (ICH) is the most feared and devastating complication of oral anticoagulation, with high mortality and disability in survivors. Oral anticoagulant-related ICH is increasing in incidence, most likely in part due to the increased use of anticoagulation for atrial fibrillation in the elderly populations with a high prevalence of bleeding-prone cerebral small vessel diseases. Risk scores have been developed to predict bleeding, including ICH, as well as the risk of ischaemic stroke. Recently, attention has turned to brain imaging, in particular, MRI detection of potential prognostic biomarkers, which may help better predict outcomes and individualize anticoagulant decisions. Cerebral microbleeds (CMBs)-small, round areas of signal loss on blood-sensitive MR sequences-have been hypothesized to be a marker for bleeding-prone small vessel pathology, and thus, future symptomatic ICH risk. In this review, we outline the prevalence and prognostic value of CMBs in populations affected by AF for whom anticoagulation decisions are relevant, including healthy older individuals and survivors of ischaemic stroke or ICH. We consider the limitations of currently available evidence, and discuss future research directions in relation to both prognostic markers and treatment options for atrial fibrillation.