The case report describes a 54-year-old woman who developed increased intracranial hypertension due to chronic dural venous sinus thrombosis in the absence of any significant comorbidity. In the years preceding diagnosis, the patient underwent routine diabetic retinopathy screening; however, gradual loss of optic cup and disc swelling was only noted retrospectively after marked papilloedema was discovered at an optometry visit. The patient made a full recovery once diagnosis was established. The authors present the case as there is an unusual availability of routine photographs demonstrating the natural history of papilloedema before medical intervention. The images show that a traditionally late sign of papilloedema, loss of cup, can be the sentinel abnormality. This finding could have clinical implications and reinforces the need for clinicians to compare investigation results with historical patient data.