The “Rule of the Pupil” states that when aneurysms compress the oculomotor nerve, a dilated or sluggishly reactive pupil will result. In previous decades, when cerebral angiography was required to detect an intracranial aneurysm, the “Rule of the Pupil” was used to determine the relative risk of angiography and the likelihood of aneurysmal compression in patients with third nerve palsies (3NPs). Noninvasive imaging including computed tomography angiography (CTA) and magnetic resonance angiography has become readily accessible and can detect all aneurysms large enough to cause 3NPs. It is therefore recommended that all patients with 3NP undergo neuroimaging regardless of pupil status because the consequences of missing an aneurysm are high. The question therefore remains as to whether the “Rule of the Pupil” still has relevance in today's era of modern neuroimaging. We describe a 73-year-old man who developed a left complete, pupil-sparing 3NP and was found to have a paraclinoid meningioma in the left cavernous sinus. As compressive lesions are expected to impair the iris sphincter muscle, no intervention was recommended and his 3NP spontaneously improved within 3 months. We also describe a 54-year-old woman with diabetes and a complete 3NP with a dilated, nonreactive pupil. Initial CTA was reported as normal, but re-review of imaging revealed a posterior communicating artery aneurysm and immediate intervention to coil the aneurysm occurred. The “Rule of the Pupil” is still important in the modern neuroimaging era as demonstrated in cases of incidentally found lesions along the course of the oculomotor nerve and missed radiological findings.