When a cystic structure in the posterior fossa increases in size, the accompanying increase in pressure may cause it to herniate upward through the tentorial hiatus. In our experience this happens most commonly with a dilated trapped fourth ventricle secondary to infection or intraventricular hemorrhage. However, herniation of an arachnoid cyst or a Dandy-Walker malformation through the tentorium may also occur. When herniation occurs, the cystic structure assumes a "keyhole" configuration, indicating that it is trapped and that surgical intervention is necessary. Five cases are presented that illustrate this point, including two patients with dilatation of the fourth ventricle secondary to hemorrhage, two patients with Dandy-Walker malformation, and one patient with an arachnoid cyst.