So this could be an issue on a system running Smoothwall.
Here is the solution:
- Create a new whitelist policy for ‘Connect for Chromebooks’ under Guardian > Webfilter > Manage Policies. Make sure you drag it right to the top
- Create a do not inspect policy for ‘Connect for Chromebooks’ under Guardian > HTTPS Inspection > Manage Policies. Make sure you drag it right to the top
- Add a authentication exception for ‘Connect for Chromebooks’ under Web Proxy > Authentication > Exceptions
The easiest thing I found is just to create these policies from scratch and naming them accordingly as opposed to adding them to some random existing policy!