Exchange 2013 Certificate error

Hi All,

OK, I have installed on a clean server, a fresh, clean installation of Exchange 2013 (CU8).

The local network is running on a .local

As I've done many times before, once I've done the initial setup of Exchange, there are the powershell commands that I execute to rename the virtual directories.

Set-ClientAccessServer -Identity "DWEX" -AutodiscoverServiceInternalUri ""
Set-OABVirtualDirectory -Identity "DWEX\OAB (Default Web Site)" -InternalUrl ""
Set-WebServicesVirtualDirectory -Identity "DWEX\EWS (Default Web Site)" -InternalUrl ""
Set-ActiveSyncVirtualDirectory -Identity "DWEX\Microsoft-Server-ActiveSync (Default Web Site)" -InternalUrl ""
Set-OWAVirtualDirectory -Identity "DWEX\owa (Default Web Site)" -InternalUrl ""
Set-ECPVirtualDirectory -Identity "DWEX\ecp (Default Web Site)" -InternalUrl ""

These all executed successfully

I've obtained a certificate from a 3rd party and the SAN names featured are, etc

OWA both internally and externally works fine (no certificate errors).

Outlook 2013 clients do autodiscover as expected, but the Outlook gives a certificate error when we start Outlook every time.

"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 dwex.dw.local.  Outlook is unable to connect to the proxy server (Error Code 10)".

dwex.dw.local is the Exchange server name.

Clicking OK clears the error and Outlook continues to work fine.

I've done this setup a number of times but never encountered this error.

Running "get" commands on the virtual directories all return the expected directory name (ie etc)

When clients ping, it returns the correct LAN IP address.

Any ideas?

Thanks in advance!
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Simon Butler (Sembee)ConsultantCommented:
I don't see the change to Outlook Anywhere.
Exchange 2013 only uses Outlook Anywhere for connection.

The other option is to do an Autodiscover test and see what URL you missed.


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JamieD71Author Commented:
Hi Simon,

Reading into this, it seems as though I need do need to modify these.

I ran get-outlookanywhere and it returned ExternalHostname as but the InternalHostname was dwex.dw.local.

Should InternalHostname also be, bearing in mind that I've got split DNS and internal clients do resolve against dwex.dw.local...

But digging around, the suggestions seem to be something along the lines of
Set-OutlookProvider EXPR -CertPrincipalName

This sound right?  Should it also be set for EXCH as well?

Thanks again and I'm impressed with a Sunday response :)
Simon Butler (Sembee)ConsultantCommented:
You need to do both the internal and external URL. I would also do the set-outlookprovider as well.
The Autodiscover test is key here - that will tell you whether you have missed anything.

JamieD71Author Commented:
Hi Simon,

All resolved.

What actually prompted me was your site here: and in particular, the checking of Outlook Anywhere URLs (and autodiscover).

I'm somewhat baffled, since I distinctly recall setting the correct internal URL...  And I don't know why it changed...

Many thanks for your help here and on your site :)


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