I am a sophomore information systems and technology student, and I am setting up a Squid transparent proxy. It filters everything it needs to (I work at a boarding high school, so pornography is a major concern).
Everything was working fine until I found out that it causes Windows Update to fail. Running a tail -f on the access log shows that the Windows Update traffic is in fact being redirected through the proxy.
The only traffic redirected through the proxy is HTTP; HTTPS passes through port 443 as it should. Why is Windows Update of all things not secured...?
As a result, I am concerned that I have set up the transparent proxy incorrectly
Here are my configuration files, and an explanation of what they are for.
eth0 is the outside NIC and eth1 is the squid proxy, DHCP server, and gateway for the network.
The only way I could get the internet to work internally was using the "network-config" utility, which would be nice to get rid of if I can.
TL; DR: My squid transparent proxy is causing Windows Update to fail, and I'm not sure what I can do about it. Help.