Outlook - Office365 - Proxy

[Trapper]

Hi Folks,

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.

Any ideas?

Strangely enough Outlook on Server 2012 works fine.

[MicrodigitUK]

Hi Folks,

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.

Any ideas?

Strangely enough Outlook on Server 2012 works fine.

1 Create a proxy exception to bypass the proxy for autodiscover.yourdomain.com in IE proxy configuration on workstation.

2 Create a DNS record on your onsite DNS server called autodiscover.yourdomain.com that points to the dns address of 365 autodiscover address.

[Trapper]

I'm afraid this has been setup since deployment. No joy.

[OutLawTorn]

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.).