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The decision to resume anticoagulation after intracerebral haemorrhage is a major clinical challenge, with current evidence offering limited guidance on balancing thrombotic and haemorrhagic risks. We present a case that highlights the intersection of multiple rare but clinically significant conditions against a background of prothrombotic risk. The patient’s course exemplifies the complex interplay between thrombosis and bleeding and the therapeutic dilemmas surrounding the timing and choice of anticoagulation. Current evidence, derived largely from observational cohorts and small randomised trials, supports a reduction in ischaemic events with anticoagulation but consistently demonstrates increased haemorrhagic risk, with limited advice on how best to individualise decisions. This case underscores the importance of multidisciplinary management, shared decision-making and the pressing need for personalised strategies in navigating anticoagulation after intracerebral haemorrhage.