I have a Linux system behind the Astaro firewall (7.005) using the HTTP proxy in Transparent mode. Up until last night, it was running Debian Lenny (Test) for AMD64. Last night I switched to Kubuntu 7.04 for AMD64 (based on Debian, of course). With both, the apt tools don't work through the proxy. It took me quite a while to figure out what was going on (at first I thought that the Debian developers broke something!).
When I realized that the proxy was causing it, I tried disabling just about everything in the proxy, and I added the update sites to the list of exceptions. It doesn't seem to be any particular feature in the proxy, but the proxy itself. When I disable it, and use a packet filter rule instead, all of the apt tools ("aptitude update", synaptic, etc.) work just fine.
What's odd about the way it breaks is that it doesn't completely fail; some package downloads fail with MD5 checksum errors, sometimes they fail with some error about having the wrong size, and sometimes there are other errors. Usually, even just an "aptitude update" fails, and even if it works, it takes a VERY long time to work.
For now, I have a workaround, but I don't like it much. I changed the proxy to be in Standard mode, and set my browsers on the Windows XP and Linux systems to point to the proxy correctly. Then, I made a rule to allow port 80 traffic from the Linux box so that I can still get the proxy benefits like content filtering and anti-virus checking, but allow my updates to work.
Like I said, I'm not happy about this situation, and I'm hoping that I can get this issue resolved so that the Debian "apt" tools will work through the Astaro HTTP proxy. I find it hard to believe I'm the only person in the world using Astaro 7.005 with the HTTP proxy with Debian systems behind it. Maybe I'm screwing something up somewhere.
Any ideas? Maybe a fix is on the way in a new version of Astaro?
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