Today I was somewhat dismayed by proxy settings under windows programs, it seems to be a complete clusterfxxx.
So some programs react to wpad settings, some use the winhttp settings which you can set with netsh, some ignore wpad settings or prioritize them over IE settings or IE settings over wpad.
It doesn't make firewall configuration easier when you combine this with Microsoft's proprietary technologies for authentication and their use of vast cdn networks for scalability.
It took me ten hours today to debug a couple of problems. If we hadn't had our SIEM, giving me visibility into the system, it would have taken even longer.
Oh and as far as I can tell Microsoft Windows logs only huge amounts of irrelevant data, lord forbid that they should include an indication as to why authentication is failing.
Grumpf!
#adayinthelife