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Outlook 2010 autodiscover settings combined with automatically detect proxy settings. Does not respect proxy exclusions, never finds cas server

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Hello all,

I currently have the following issue.

We have upgraded to exchange 2010 in our organization and i'm about to migrate all users across, however we have the issue that we cannot set the out of office and setting up new profiles seems to not work unless we've turned all proxy settings off. I've pinpointed exactly where our issue lies as well. It is the following.

We use a wpad file for our internet configuration for all clients. this works great, and all exclusions for internal urls are added and work well also. HOWEVER during the outlook 2010 autodiscover process the exclusions are flat out ignored. At NO OTHER TIME are these exclusions ignored, to confirm this, I configured a folder in outlook that points at an internal webserver and opens that page. It works. I can also resolve the urls of the cas.domain.corp and the specific server names.

To further confirm that my wpad file configuration is OK, I download it to the c: drive. I then point internet explorer at that exact file and then Outlook autodiscover operates completely normally all functions work. I then point internet explorer back at 'automatically detect' or alternatively 'use an automatic configuration script' and the issue is back. Ive even confirmed using wireshark that when autodetect is used, outlook sends all internal server packets externally to our cloud proxy (which should be bypassed with the exclusion list).

This process is maddening, because I went through about 5 hours of troubleshooting with Microsoft support, exchange support and they concluded that 'it's an IE problem you should call them'. This is preventing us from migrating our entire organization to exchange 2010, so if anyone could help me I'd be eternally greatful.

versions

outlook 2010 sp2

exchange 2010 SP3

IE 9 or 10 (both versions tested, both versions exhibit same problem)


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