Aha, this all makes sense. I can work around it, but you're right, it's
horribly confusing for new users.

What would be best IMHO, is if the suite of apt frontends (synaptic,
update-manager, etc) handled the "407 Proxy auth required" response
gracefully and prompted for credentials.

-- 
Synaptic doesn't play nicely with proxy-auth
https://launchpad.net/bugs/56293

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