Why is my Mac user getting "Protection Disabled" when it is enabled?

I had a similar issue on the Mac. The problem ended up being Webroot was losing the keycode. Check the My Account section on the right and make sure it shows a keycode. It will display like this SA93-****-****-****-****. If it doesn't display, you'll need to either re-input it or re-install the software. If you're still having issues, contact support.

Unfortunately no luck.
We tried reapplying the keycode (even though it shows already) and it just said it was "controlled from the web console". The mac is reporting in, says it's protected on the web console, and in the "My Account" on the mac, it shows the active subscription - but the explanation ding "!" is still showing with the big "Protection Disabled" in the window (as shown in the above screenshot).

Dumb question, did you try clicking the "Enable Now" button?

Also, you could try reapplying the keycode from the console or if you haven't tried yet, uninstall and reinstall.

Clicking the enable button shows the same "controlled from the web console" message then does nothing. As mentioned in the previous post, we tried re-applying the key-code.

I'll try a reinstall later today, but this was a fresh install, pretty straight-forward. The bugger is it says "Some security settings that protect your mac are disabled" - WHAT SETTINGS?!!!? Everything's green!

If you dig into each section you might find that something is disabled although the section as a whole is enabled. Forgive me, I'm behind on my knowledge of what the Webroot version has access to in the console. Can you apply a policy to the endpoint via the console? If so, are you using the default policy applied to this endpoint by console or did you create your own?

Congrats on figuring it out @chriseaton!