The IT department just made my life a little bit harder again: they introduced a manual HTML login page for all websites they have not "classified". This means that all the applications which try to access unclassified websites for e.g. downloading plugins do not work. Examples: Eclipse plugin installation, Maven builds etc.

What would be the easiest workaround for this? The best I've come up with is try to extend/customize Ruby's httpproxy.rb that comes with Webrick. I would automate the manual login process whenever that login response page is detected. This sounds quite painful, and I think there might/should be simpler options?