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Our application can connect to Internet only directly or via SOCKS proxy. Unfortunately we can only access the Internet via HTTP proxy protected by NTLM authentication. Is there any SOCKS server that chains outgoing connections via HTTP proxy? NTLM authentication support is mandatory.

We've checked antinat but found nothing about NTLM there.

Other solution could be to use SSH acting as SOCKS proxy chained to Proxytunnel, but this requires to have an additional server out of our network to act as SSH tunneling endpoint.

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I heard once of an Apache module that listens to connections and then chains them to a proxy server, but I don't know if it supports NTLM – golimar Feb 25 '12 at 10:10

SOCKS is a TCP/UDP proxy, which means that it can't be arbitrarily passed through an HTTP proxy. ntlmaps and cntlm are HTTP proxies which do NTLM authentication. I think your only bet is to try use iptables to transparently proxy traffic via ntlmaps/cntlm (I don't know if they support being used in transparent mode; if not you may need to add Squid into the mix as well).

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