Already did that. :) Although since I'm doing SSL offload, the IIS certs 
shouldn't matter.

Senior Systems Engineer
317.447.6033 (office)

From: [] On 
Behalf Of Debora Gilbert
Sent: Saturday, October 15, 2016 8:58 PM
Subject: Re: [Exchange] Outlook certificate error?


Check your IIS certs and make sure you're not using a self signed one.


From: <<>> 
on behalf of Damien Solodow 
Reply-To: <<>>
Date: Wednesday, October 12, 2016 at 14:46
To: "<>" 
Subject: [Exchange] Outlook certificate error?

We've been intermittently finding an odd issue; Outlook will pop-up the 
following message:
There is a problem with the proxy server's security certificate.
Outlook is unable to connect to the proxy server FQDN.
(Error Code 80000000).

Clicking Ok on the message gets rid of it and Outlook acts normal. I've looked 
at the Outlook connection status while the message is onscreen, and it shows 
successful connections to HTTPS as well as usually a disconnected one for the 
mailbox. OWA doesn't show any cert issues, and it's sporadic.

Exchange 2010 SP3, CU14 on Windows Server 2008 R2 SP1.k
Clients are Windows 7 SP1 x64, with Outlook 2013 SP1 x86.
Our CAS servers are behind an F5-LTM doing SSL off-load.
This isn't a new setup; the issue start occurring in the couple months as far 
as I've been able to determine.

Senior Systems Engineer
317.447.6033 (office)
550 East Washington Street
Indianapolis, IN 46204<>

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