We've talked with Jamf about this and it seems to be a known issue with 9.99. All the config profiles, especially wifi payloads, will get stuck at pending or take hours to push. It seems to be hit and miss, but it's the vast majority of clients scoped that have this issue. Has anyone else run into this or know of any workaround until the next version comes out?
Posting just to be made aware of additional posts to this thread. We're not on 9.99 yet, but were supposed to be upgrading soon. I sure hope that release didn't create problems with Config Profile pushes.