Question

Work around for certificate errors on internal clients using Ex2K7 via Outlook 2K7?

Asked by: stedwardsitdept

This may be a bit long winded so my apologies in advance!
We have a rather sticky problem with certificates on our new Exchange 2007 Client Access server set up. We are currently in the process of trying to migrate from Ex2K3 to Ex2K7. We've moved a few test clients over to the new Ex2K7 server and they are all getting certificate errors when Outlook 2007 starts up on domain joined machines (internal clients). The error states that the site name that Outlook is looking for is different from what is on the cert. And it is correct. Here is the whole sorry saga of our certificate tragedy:
We are a school in the UK. We have a publicly registered domain name that ends with .sch.uk. Our internal/private AD domain name is nearly identical to our public domain name and also ends in .sch.uk (dont ask, this was before my time) and looks very much like a public domain name. Because of this, we were unable to find a single commercial certificate provider that would include our internal FQDNs to any UCC certificate we wanted. In the end, we ended up purchasing a Digicert UCC cert that had only our external FQDNs for the CAS server and autodiscover services. We tried to work around this problem by enabling both our commercial cert as well as the default MS cert that ships with Ex2K7 which we added all of our internal FQDNs to. The hope was that the external clients would be able to use the commercial cert, while the internal clients would be able to use the default simple cert. This seemed to work for a brief time, but after a few weeks, Outlook 2K7 on the internal clients began ignoring the internal certificate and started using the commercial cert which, of course, didn't have any of the internal information on it and hence they started getting the certificate error on startup. After much wrestling with this issue, we made the decision to register our internal domain name so that we could provide Digicert with a "whois" for it and they would then be happy to add our internal FQDNs to our commercial cert. However, I then spoke to Nominet and was told that we could NOT register our internal domain name because it has the .sch.uk suffix and since we already have one .sch.uk domain name registered, we can't register another one.
We've been given two options by certificate providers, domain name registrants and Nominet alike:
1. Rename our external domain name so that it is the same as our internal domain name
2. Rename our internal domain name to use a suffix like .int or .local
Neither of these options is even slightly appealing to us so we are desperately trying to find a work-around.
I am now aware that having two active certificates running on the same CAS server is not supported. Is it possible to have two CAS servers in the same organisation and to force internal clients to use a specific one for autodiscover? If so, we could set the two up and just have the Digicert commercial cert on one for external access and have the MS default cert enabled on the other for internal access.
Any other thoughts or ideas would be greatly appreciated.  Many thanks,
Adam

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Asked On
2009-11-03 at 02:37:01ID24866592
Tags

Exchange 2007

,

client access server

,

certificate

,

Outlook 2007

,

site name

,

error

,

mismatch

Topic

Exchange Email Server

Participating Experts
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Points
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Comments
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Answers

 

by: saakar_raoPosted on 2009-11-03 at 05:09:13ID: 25728521

Thanks for that wonderful explaination, I wish I could more and more questions that would be as descriptive as you are

What I understand from the issue that you are facing is referred in the below mentioned KB article

Security warning when you start Outlook 2007 and then connect to a mailbox that is hosted on a server that is running Exchange Server 2007 or Exchange Server 2010: "The name of the security certificate is invalid or does not match the name of the site"

http://support.microsoft.com/kb/940726

 

by: stedwardsitdeptPosted on 2009-11-03 at 08:12:41ID: 25730422

saakar_rao
Thanks for that. I do try to put in as much relevant detail as possible to aid in understanding the issue.
And thanks again for making me take another look at that MS KB article! I've looked at that article in the past but as soon as I got to the part that states "you must add a host record for the mail host name that is mapped to the internally accessed IP address of the CAS server", I quit reading the article because there was no way we'd ever be able to do something like that without using a split DNS configuration which simply woudn't work in our environment. However, this time around I spotted the last bit in the "More Information" section about changing the AutodiscoverServiceInternalUri attribute of the SCP using the Set-ClientAccessServer cmdlet and decided to give it a try. Exchange sets this value to https://<cas server FQDN>/autodiscover/autodiscover.xml when you install the first CAS server. I used that cmdlet to change it to https://<our external FQDN>/auto...etc. and then tested an internal client and hey-presto, problem solved! Tested external access and all appears to be well. Can't believe the fix was so simple after all the madness we've been through with this!
Will mark your entry as the accepted solution. Cheers!
Adam

20120131-EE-VQP-002

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