I’m back with some more information. The issue here was not that I needed to have a skeletal mesh. The actual issue was that the dropdown on a static mesh called “Collision Complexity” causes overlap events to not trigger properly when it is set to “Use Complex Collision As Simple”. Volumes using the built in “Shape Collision” (or any of it’s children) seem to only check against simple collision and the checks they use don’t seem to work properly when the simple collision is overridden by complex collision. Adding simple collision and not only relying on complex collision fixes the issue.