Exchange 2007: Troubleshooting SSL Cert

I just migrated an Exchange 2003 server to 2007 (Server 2003 to 2008) and would like some advice on aligning the newly installed SSL certificate.

When this server sends mail to the internet it is identifying itself as <ServerName> rather than <> . This is in contradiction to the SSL cert we purchased, and all configurations. I'd like to have this sync up, as AOL is rejecting our mail. I'm concerned that corporate caching name servers will populate the mismatch and we'll get bounced email for a few weeks before the cache name servers refresh.

Your help is greatly appreciated.

Who is Participating?
you change this on the send connector, but you also need to make sure your rDNS (PTR) record is the same as whatever you change it to. Go into Exchange --> Org config --> Hub Transport --> Send connector, select the one responsible for internet mail and change FQDN.

Also see my blog entries on rDNS and on DNS data and SMTP in general:

Satya PathakLead Technical ConsultantCommented:
Suppose we want to create a UCC self-signed certificate. We will require the following names:

#NETBIOS name of Exchange: EX-2k7 (example)
#Internal FQDN: (example)
#External FQDN (Public name): (example) (use nslookup/ping to verify the external FQDN)
#Autodiscover name: (example)
#SubjectName: (example)

In EMS, run the following command to generate the new self-signed certificate:

New-ExchangeCertificate -FriendlyName "SelfSigned Cert" -SubjectName "" -DomainName EX-2k7,,, -PrivateKeyExportable $True

Next enable the certificate with Enable-ExchangeCertificate cmdlet. Enable atleast IIS and SMTP.

Enable-ExchangeCertificate -Thumbprint xxxxxxxxxxxxxxx -Services POP,IMAP,SMTP,IIS

Next verify certificate has been installed using EMS/IIS Manager or both. (Sometimes you may have to remove the certificate and then install/enable certificate again).

Some important points:

1. If you are creating a self-signed certificate, it is always better to create one that has all the subject alternative names specified above. This will prevent any certificate security warnings related to name mismatch. If you are creating single-name self-signed certificate, you would have to modify internal URIs of multiple virtual directories as explained in KB940726. The other benefit of multiple SANs is avoiding event 12014 and similar events.

2. Autodiscover for non-domain joined machines will work only after record is created in external DNS

3. You will have to install the certificate in the trusted root on client machines else you will receive a certificate warning. On Vista machines, you will have to run IE with elevated privileges to be able to install the certificate when you open OWA.

4. You can use group policy to install the certificate in trusted root (applicable only to domain joined machines). Copy to file the self-signed certificate (ideally in .p7b format) and then edit the default domain policy and import the certificate into "Computer Settings\Windows Settings\Security Settings\Public Key Policies\Trusted Root Certification Authorities". No user intervention is required once you do this. (Users would have to install the certificate themselves on non-domain joined machines).

5. SBS2008 Information: When you install SBS 2008, setup Internet Address wizard uses self-issued certificate by default. You will find it is "Issued to" "external FQDN" of the server and "Issued by" would be "Internal FQDN-CA" (SBS setup configures CA by default). When the wizard generates the self-signed certificate, it also generates a Certificate distribution package. The package (Install Certificate is located under one of the default shares named Public (C:\Users\Public). Another point to remember about SBS2008 is that the default certificate is single-name certificate and if you create a new one with multiple subject alternative names using the procedure above, you will receive a warning while enabling SMTP on the certificate. This warning can be ignored. You can verify availability of STARTTLS verb using Telnet.
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