I've tried Outlook 2010 and 2013 on a Windows 8 Enterprise machine and it will not connect to the Office 365 Exchange server.
Go home on a direct connection - no problem. VPN to work and turn the proxy settings on - no dice.
Strangely enough Outlook on Server 2012 works fine.
I'm afraid this has been setup since deployment. No joy.
Does the proxy require authentication?
Office 2007/2010 will use the default system proxy settings, but doesn't ask for auth (if required) and so things like Exchange over HTTP wouldn't work. We found that if you run a local proxy (eg an application on your computer) which doesn't need auth, you can then forward traffic to your site proxy which does and have it "inject" the authentication. "Proxomitron" is a little free application which worked for us (Proxomitron.Info ...the Webhiker's Guide to Proxomitron.).
Voodoo thread resurrection!
Turns out that MS finally released the patches for this a month or so ago. And you still need a registry fix for it.
Patches for Windows and Outlook are out on Windows Update, the reg fix is:
Note In this key path, the placeholder x.0represents 15.0 for Outlook 2013 and 14.0 for Outlook 2010.
On the Edit menu, click New, and then click DWORD Value.
On the Edit menu, click Modify.
Type 1, and then click OK.
Exit Registry Editor.
You'll need to create the RPC key.
Then it works. From what I've read on Technet this behaviour is by design! Microsoft obviously feel manually entering the proxy and exceptions to be a depreciated method and we should all use PAC files.
Out of interest, what is the Patch number?
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