Exchange SSL Certificate Issue

Okie doke guys, got an odd one,

Self-cert ssl certificates expired on our internal exchange server, and the old DC has long since been removed (badly it would seem).

As re-self-certing wasn't an option, i ordered a real SSL cert from RapidSSL, and applied it.

I followed the guide below:

HOWEVER, i'm still getting an SSL mismatch error (screengrab attached) despite it being applied everywhere i can think/see.

If i hit the OWA site associated with the SSL cert, all is well and it works fine. If i try and use Outlook though, i get the above error.

Any help on this would be greatly appreciated!

Server is 2008R2 Standard, running Exchange 2007 Standard
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MAS (MVE)EE Solution Guide - Technical Dept HeadCommented:
This is due to the name mismatch in the certificate.
Do you have the below names added to the certificate.
Exchangeserver FQDN(Optional).

Are you getting this error when opening outlook as well?
iainmacleodAuthor Commented:
Negative, certificate is just for

The screenshotted popup ONLY occurs during opening of outlook (locally or on vpn), and once it has been allowed, it does not come back until one closes outlook
MAS (MVE)EE Solution Guide - Technical Dept HeadCommented:
You need minimum 2 names in the certificate
i.e. (comman name)

and configure the internal and external URLs using the attached file
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Please refer this URl

Hope this helps.

iainmacleodAuthor Commented:
Looking at link in Tony's post, does this get around the fact i don't have 2 records in the certificate?

The line "Host: URL for redirection. This URL may be the Outlook Web Access (OWA) URL because the resolved IP should be the same as the Autodiscover service. Additionally, this may vary from deployment to deployment."

I've understood that as using the internal dns name (the dns server i'm applying this to is internal only, all our external users use OWA)?
Simon Butler (Sembee)ConsultantCommented:
You can get around the problem for internal users easily.
Just reconfigure Exchange and use a split DNS system.

However for external users, your external DNS provider must support SRV records, so you can create the required SRV record.


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iainmacleodAuthor Commented:
Not quite following you there Simon?
Simon Butler (Sembee)ConsultantCommented:
What is there that isn't clear?
You are configuring Exchange to use the external host name internally, which allows you to use the certificate you have, but if you want to support external clients (Outlook Anywhere) then you need to have an Autodiscover solution in place. For a single name SSL certificate that means SRV records.

iainmacleodAuthor Commented:
I have been asked to explain the low score I gave to this question... I may have been having a bad day but I did not initially see the Links to Those certainly do make the solution more comprehensive.
My apologies, how should I regrade this solution?
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