Detachable endovascular coils have become a common treatment strategy for carotid cavernous sinus aneurysms (CCAs), but previously unrecognized postprocedure complications may emerge as longer follow-up data are accumulated. In this report, the authors document the first known cases of delayed cranial neuropathy following CCA coiling in 3 patients, all of whom present at least a year postprocedure without aneurysm regrowth. The potential mechanisms underlying this syndrome are discussed as well as their implications on the selection and optimal endovascular management of CCA patients. Three previously healthy females aged 50, 60, and 62 underwent CCA coiling at our institution and subsequently developed ipsilateral cranial nerve palsies at 56, 28, and 14 months, respectively, post-procedure. At presentation, all 3 patients had a new, recurrent area of flow in their CCA without changes in aneurysm size. One patient declined further treatment. In the other 2 patients, a stent was placed across the aneurysm neck, and one patient underwent additional coiling. Unfortunately, all 3 patients remained symptomatic at their latest follow-up. Because of the intimate anatomic environment of the cavernous sinus, neural elements within it may be particularly susceptible to persistent mass or dynamic effects exacerbated by remnant or recurrent flow across the neck of a coiled aneurysm. These 3 cases prompted the authors to advocate for more aggressive efforts to achieve and maintain CCA occlusion. Furthermore, when such efforts are unsuccessful, consideration of traditional carotid occlusion strategies with or without bypass is warranted.