Question Odd Issue With Ops.json

After updating to 1.8.3, I am having the craziest issue when it comes to interacting with a sign. For some reason when I have a specific user opped, the second user on the server cannot interact with a sign and all of their granted permissions ('*') are broken. I am using WorldGuard and PermissionsEx. I have tried turning debug on for both of these plugins and there are no warnings or errors about the interaction with the sign. When I remove that specific user from ops.json, the other users permissions are fine again and they can interact with the sign. When I op the second user, the first users permissions are fine and they can interact with the sign just fine. Can anyone think of any reason why this would be functioning this way?

Full plugins list:

Lockette
Multiverse-Core
Multiverse-Portals
OrePlus
PermissionsEx
PreciousStones
Spectate
TerrainControl
Vault
WorldBorder
WorldEdit
WorldGuard