I have been using polipo as my proxy server and recently, it has been developing some weird problems. For one thing, it sometimes refuses to connect to websites without any errors on the client side except for time-outs. I know that the sites are up because I can connect to them if I bypass polipo.
The reason that I use polipo is because of resource requirements – much less than say, squid. As an upstream web proxy, it works really well. I have gotten better results out of it than squid but I simply put that down to my lack of squid config-fu. Polipo is much easier to configure as there are less options to play. However, it is also a plain vanilla proxy and does not try to become the proxy for everything as squid does.
After some investigation, I got a clue from the polipo logs – that it was timing out as well with the following message:
Host ftp.osuosl.org lookup failed: Timeout (131072).
This confused me because it was obvious that the website was up and working. So, I dug around and found out that polipo uses its own DNS resolver by default and not the system resolver. The reason that it does this is in order to obtain the TTL information on the domain directly. However, the information still comes from the same DNS server either way.
Turns out that it was a networking problem. By default, polipo would return the AAAA record instead of the A one if both are present. It is designed to prefer IPv6 over IPv4. My home network is IPv6. This can be controlled with either of the following options:
dnsQueryIPv6 = no
dnsQueryIPv6 = reluctantly
Since I have not yet enabled IPv6 support through my gateway, I decided to just disable IPv6 for polipo entirely. I might turn it back on once I get IPv6 up at home. I really need to get down to activating my Hurricane gateway tunnel and writing a guide for it.
Technical Intercourse 