For #2 the error from SQUID's error page that I see is like this: ERROR The requested error was encountered while trying to retrieve the URL : / Invalid URL Some aspect of the requested URL is incorrect. Some possible problems are: Missing or incorrect access protocol Missing hostname ... So I am leaning into thinking of two things. My VPN routing to SQUID server is missing something which is causing the request to be bad. Secondly access denied logic is happening before the request validation. I suspect in VPN client's case intercept or not it will fail (even without access denied problem). Thanks,