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MS Outlook not connecting to local Exchange Server when proxy is enabled in the Browser.

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Hi,

I am using exchange 2010 and MsOutlook 2007, 2010, 2013 in my network. Both are on the LAN Segment of the Firewall.

We have deployed Watchguard XCS as Anti-Spam Gateway in the DMZ zone of the Firewall. We are using the same XCS as Proxy Server for internet access for the users.

When i enable the users pc with proxy setting in the browser with XCS ip address, my outlook starts prompting for username and password and doesn't connects to the exchange server at all.

But when i disable the proxy settings in the browser my outlook connects my exchange server perfectly.

After some diagnostics from the xcs support, they are saying that outlook is trying to connect to the xcs instead of exchange server when proxy is enabled. even after adding the exchange server ip in the local browser's proxy exception the problem persists.

Also tried with outlook anywhere, with no success.

Please help me.


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