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Introduction We present a case demonstrating the difficult balancing act of bleeding and thrombosis following intracranial haemorrhage (ICH).Case description A 60-year-old woman presented following a thunderclap headache (TCH) and left hemiparesis involving her face, arm and leg. She had presented twice to the emergency department following TCHs during defecation in the prior 48 hours, however, was discharged home following negative computed tomography (CT) and CT angiography (CTA). This time, CT brain (CTB) demonstrated a right basal ganglia haemorrhage. She had been on warfarin since 2012 for management of anti-phospholipid syndrome (APS) and homozygous MTHFR mutation. INR on admission was 1.8. Warfarin was suspended and reversed. Given recurrent TCH, she underwent digital subtraction angiography (DSA), which was suggestive of reversible vasoconstriction syndrome (RCVS). Verapamil was commenced. On day 13, she had a saddle pulmonary embolus (PE) on CT pulmonary angiogram. She was haemodynamically stable without right heart strain; therefore, did not undergo thrombectomy. An inferior vena cava filter was inserted, and on day 14, she was commenced on enoxaparin 40mg twice daily. On day 25, this was increased to 60 mg twice daily. Given she did not have triple positivity on APS investigations, a plan was made to switch to a direct oral anticoagulant after two further weeks on enoxaparin. CTB remained stable and on day 35 she was discharged to a rehabilitation hospital.Conclusion Further guidance is required to manage the timing of anticoagulation in the post-ICH period, especially for patients with multiple comorbidities who cannot forego anticoagulation.