Just migrated Exchange 2010 to 2013 and imported the certificate from 2010. I have done the following:

1. Modified all virtual directories to point to mail.domain.com

2. Changed autodiscover internal access to point to mail.domain.com

3. Changed OutlookAnywhere to point to mail.domain.com

Since I did these three, autodiscover will change the name in the proxy settings to mail.domain.com for the Outlook profile. The certificate message upon opening Outlook will go away, but it still complains about the proxy server with Error Code 10.

I created a new profile and this error went away entirely. Autodiscover grabs all the correct settings for a new profile In either profile, E-Mail flows with no issue. Just an annoying popup.

Without creating new profiles for everyone, can I get rid of this popup?

Full Error Message Text:

There is a problem with the proxy server's security certificate. The name on the security certificate is invalid or does not match the name of the target site ex2013.domain.local. Outlook is unable to connect to the proxy server. (Error Code 10).

Any ideas?

Thanks!

• Edited by Rohrbach21 17 hours 34 minutes ago

If you're sure new profile works, you can use the 'Repair...' button in the  Account settting page to fix the existing profile.

Nope. I still get the error message, but the certificate and all settings populated in new profile are correct. Old profile is also correct. I get no error message about the certificate not matching, only the proxy error.

Hi,

Please confirm whether the issue happens to all users or specific users to narrow down the issue.

You can run the following command to check your certificate settings and outlook anywhere on Exchange server:
Get-ExchangeCertificate | fl

Get-OutlookAnywhere | fl Identity,*host*,*auth*

Regards,

David 

Please post the screen capture of the error message, and indicate when do you see it exactly.