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I can confirm this bug. It's a headache, because I'd like to use apt-proxy to let my high school classroom full of machines tax our overburdened school connection less. It works brilliantly except when it hangs spectacularly, and I ideally want a server I can just forget about.
I'm trying out Elijah's workaround today. If Elijah is right, then the bug would seem to be related to the http handling code (handled as an import) in apt-proxy.py It looks from the Sourceforge page and the project webpage that apt-proxy hasn't seen any development in years. The last CVS commit from a developer on the main component (apt-proxy.py) was 3 years and 1 month ago.
I haven't programmed in Python, but I've been looking for an excuse to learn that language. Does this seem like a bug that a (relative) novice could tackle? I need to get my feet wet with some code anyway, since I might be teaching a programming class next year. Ultimately, I'd like to find a project in Java to help with, but this one is something I use. It's a programming itch that I want scratched, to borrow E.S.R.'s metaphor.