It's been a while, and I've made some tests. This happens not only in
Gutsy Server, but also in GUI Hardy 8.04 with Synaptic and all the
updates.

The problem occurs only if using proxy-server, both when using ~/.bashrc
or apt.conf.d to set the proxy.

The sources.list is a pretty general one, i haven't made any changes to
it. I tried to experiment, and leave only a couple of lines there, but
the results were negative, proving that it's not the sources.list case.

Also, not only the Release.gpg file is downloaded thousands of times.
Rarely, but also present, much larger files, like Packages.gz are being
downloaded many-many times. And as I pay for the bandwith, this is
really disturbing.

Turning of the proxy completely solves the problem, but i can turn it
off only for testing purposes.

The proxy server is built with "Kerio WinRoute", and I think the problem
lies within this piece of software. But apt (and also Synaptic) still
lets itself download the files for thousands of times, which is not
nice.

The complete contents of the /etc/apt directory are attached.

** Attachment added: "apt.tar.bz2"
   http://launchpadlibrarian.net/16296656/apt.tar.bz2

-- 
Apt-get update is almost endless in Gutsy Server
https://bugs.launchpad.net/bugs/221884
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