While you can set up squid to do both NTLM and
fall back to basic authentication, it won't do you much good in that
case.
If I'm understand you, you are saying that squid will do client->squid
ntlm,not squid->remote proxy ntlm.
In which case he should probably use aps098?
http://www.geocities.com/rozmanov/ntlm/
In terms of getting Gentoo specifically to authenticate with an NTLM server,
I'd say there is actually no chance, unless the MS proxy specifically has
ports 873 or 21 enabled and I'm not so sure (from what I can remember of the
heathen MS proxy server I killed a few months back) that Microsoft proxy
servers (on the NT 4 iteration) support FTP never mind rsync and afaik you
need to contact the Gentoo rsync server for your initial emerge rsync
(funnily enough)!
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