After I edit/update my Extra Fields the changes are not showing on the front end. This is after deleting cache and purging even. I've tried breaking the association with the category and even that doesn't help.

Ideas?

Are you seeing the changes on the backend? And is your site using other system plugins for cache?

Yes, the edits show up in the backend when I look at the status of the categories, fields and field groups. Everything looks normal. But when I go to the frontend to create an item I don't see the updated information at all. It says the category has no extra fields associated with it.

However, when I go to add an item in the backed the updates show up just fine. It's the frontend that's the problem. I've tried clearing every cache I could find and nothing is helping. Backend is fine: edits to groups show up instantly. Front end, not so much.

Are you behind a CDN?
Also some template providers provide additional caching plugins. Check your system plugins to see if there is one.

No CDN and I'm using Rocketthemes. I don't have their cacheing turned on. Even changing to a different (non-Rockettheme) theme I still see the same issue.

Now you 've got me confused. The topic is: Extra Fields Not Showing Changes to Backend and you said

If the issue is on the frontend there is a plugin call Rocksprocket (I think) this has several options. Make sure it is configured correctly. Finally if your server is running APC cache make sure it is also configured correctly.

Not showing changes made in the backend.

I have all cacheing disabled and no change. RockSprocket it a content display module and shouldn't impact what happens when someone tries to create an item, but I checked the settings anyway, just to be sure.

While troubleshooting I figured out something... the New Item popup (in Lightbox) refreshes if I close my browser completely and reopen, but this seems to be limited to IE, latest version/hotfix and no add-ons.

So if I understand you correctly, when you change an item in the frontend using K2's form the changes are not reflected in the backend, right?

Have you tried reverting to the default K2 template?

If the problem is located in backend, please try reinstalling K2's latest version.