Hi Luke,
Try having the Ruby Console open in SketchUp when you click on any of our tools or try activating. You can find this in Windows>Ruby Console. If you see any errors that are reported, take a screenshot and send it to us or copy/paste into an email. This can help us to track down any other issues. Even in failure cases (no internet, connection failed, invalid username/password, expired subscription, etc), the window should still respond and report the issue to the user.