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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.

Squid.conf

IP Tables configuraton

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.

Any advice?

TL; DR: My squid transparent proxy is causing Windows Update to fail, and I'm not sure what I can do about it. Help.

  • Have you considered looking at the access.logs or using tcpdump to figure out what is being blocked when a computer attempts to access windows update site? Does the school have WSUS? If not, then you should strongly consider it, and then just whiteless the WSUS server. You will save bandwidth get reporting of client update status, and work-around this particular problem. – Zoredache Jul 3 '14 at 23:45
  • The reason I'm confused is that, while it is going through the proxy, it isn't actually blocking it. Also, I'm running a Debian server, not a Windows Server. – Earth Jul 3 '14 at 23:54
  • Your first step here should be looking at the logs on a machine that's failing to update. Just looking at the server side logs is unlikely to be helpful. I'm also somewhat surprised you've been put in charge of the production network... – devicenull Jul 4 '14 at 1:57
  • I chose to, lol. They've been using windows server 2000 for a long time and I knew it was time to upgrade. I offered to try, and they said sure – Earth Jul 15 '14 at 20:28

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