In my years of working behind a firewall at my day job, I've lost count on how many times I've had to configure, reconfigure and just plain experiment with proxy server configurations to get that app to work just right.
My guess is that many other developers/technical professionals out there do the same thing. Picture yourself working at a company where you have [gasp] Microsoft ISA server deployed along with Active Directory which seamlessly integrates with it. Of course you're on Windows. Because of that you may have some applications that don't allow to send NTLM credentials to the server or you prefer not to store your own credentials in code somewhere. Thus you have also installed your own proxy that uses the ISA as an upchain proxy - CNTLM.
So here's some examples:
Internet Explorer - your IT Support folks force the ISA Proxy server and exceptions (which you can't update) into IE's setting via Group Policy. This works flawlessly, except when it doesn't.
Firefox - Ok, so who still uses Internet Explorer? Firefox - I've used FoxyProxy which works some of the time. Based on the website you're visiting, trial-and-error to pick a proxy (ISA, Direct, CNTLM)
Other Browsers - If Firefox is not your thing, maybe you use Chrome, Opera, ??.
Anything Java - How many times have you typed out
IDE's - Anyone else ever seen that either Eclipse update works OR your code that reaches out to the Internet works, but NEVER both?
Other - VPN Clients, background update processes, SSH, Xmarks (and other browser plugins), etc....
So my question is this: Can you make sense of all of this? What solution have you come up with to get over proxy server hell? Do you daisy-chain multiple proxy's like I have tried to do? I've configured applications with various combinations of CNTLM, Direct, ISA, Windows system level proxy setter: proxycfg, Microsoft Firewall Client, etc... What have you done to overcome this?