Exchange Server 2010 makes use of SSL certificates for securing network communications between servers and clients. An example of this is Outlook Web App (OWA) which uses the HTTPS protocol for users connecting via their web browser (eg https://webmail.company.com/owa).
In this article:
- Introduction to SAN Certificates for Exchange Server 2010
- Enabling SAN Certificate Support for Windows Server 2003 Certificate Services
- How to Request a SAN Certificate for Exchange 2010
- Completing a Pending Certificate Request for Exchange Server 2010
Introduction to SAN Certificates for Exchange Server 2010
Traditionally SSL certificates were issued for a single name (such as the webmail name above), however this is very limiting because once an SSL certificate is bound to an IP address that IP address is not able to accept connections addressed to different names over SSL, or at least not without the name mismatch causing a warning message to the connecting client.
This became an issue for Exchange Server 2007 and 2010 because, depending on the server roles installed, the server may need to accept SSL connections to several different names such as:
- the server’s FQDN (eg ex3.exchangeserverpro.net)
- webmail and other published names (eg webmail.exchangeserverpro.net, mail.exchangeserverpro.net, mobile.exchangeserverpro.net)
- multiple DNS namespaces (eg autodiscover.exchangeserverpro.net, autodiscover.xyzimports.com)
Configuring multiple IP addresses, DNS records, IIS instances, and SSL certificates for all of the possible names in an Exchange organization would be tedious and expensive.
The X.509 certificate standard has catered for this for a long time now with a feature known as Subject Alternative Names. Basically this allows a single SSL certificate to be configured with a primary name and then multiple alternative names, making it valid for all of the required names that clients and other servers will be connecting to.
SAN certificates are available from most commercial providers however some organizations choose to issue them from their own private certificate authority. Windows Server 2008 Certificate Services supports SAN certificates by default, however Windows Server 2003 requires the option to be manually enabled first.
Enabling SAN Certificate Support for Windows Server 2003 Certificate Services
You can check an existing Windows Server 2003 CA for SAN support by using the certutil utility from a command prompt.
C:\>certutil -getreg policyEditFlags HKEY_LOCAL_MACHINESYSTEMCurrentControlSetServicesCertSvcConfigurationcaPo licyModulesCertificateAuthority_MicrosoftDefault.PolicyEditFlags: EditFlags REG_DWORD = 15014e (1376590) EDITF_REQUESTEXTENSIONLIST -- 2 EDITF_DISABLEEXTENSIONLIST -- 4 EDITF_ADDOLDKEYUSAGE -- 8 EDITF_BASICCONSTRAINTSCRITICAL -- 40 (64) EDITF_ENABLEAKIKEYID -- 100 (256) EDITF_ENABLEDEFAULTSMIME -- 10000 (65536) EDITF_ENABLECHASECLIENTDC -- 100000 (1048576) CertUtil: -getreg command completed successfully.
If there is no EDITF_ATTRIBUTESUBJECTALTNAME2 flag then you can enable it by running the following command.
C:\>certutil -setreg policyEditFlags +EDITF_ATTRIBUTESUBJECTALTNAME2 SYSTEMCurrentControlSetServicesCertSvcConfigurationcaPolicyModulesCertifi cateAuthority_MicrosoftDefault.PolicyEditFlags: Old Value: EditFlags REG_DWORD = 11014e (1114446) EDITF_REQUESTEXTENSIONLIST -- 2 EDITF_DISABLEEXTENSIONLIST -- 4 EDITF_ADDOLDKEYUSAGE -- 8 EDITF_BASICCONSTRAINTSCRITICAL -- 40 (64) EDITF_ENABLEAKIKEYID -- 100 (256) EDITF_ENABLEDEFAULTSMIME -- 10000 (65536) EDITF_ENABLECHASECLIENTDC -- 100000 (1048576) New Value: EditFlags REG_DWORD = 15014e (1376590) EDITF_REQUESTEXTENSIONLIST -- 2 EDITF_DISABLEEXTENSIONLIST -- 4 EDITF_ADDOLDKEYUSAGE -- 8 EDITF_BASICCONSTRAINTSCRITICAL -- 40 (64) EDITF_ENABLEAKIKEYID -- 100 (256) EDITF_ENABLEDEFAULTSMIME -- 10000 (65536) EDITF_ATTRIBUTESUBJECTALTNAME2 -- 40000 (262144) EDITF_ENABLECHASECLIENTDC -- 100000 (1048576) CertUtil: -setreg command completed successfully. The CertSvc service may need to be restarted for changes to take effect.
Next you must restart Certificate Services for the change to take effect.
C:\>net stop certsvc The Certificate Services service is stopping. The Certificate Services service was stopped successfully. C:\>net start certsvc The Certificate Services service is starting. The Certificate Services service was started successfully.
How to Request a SAN Certificate for Exchange 2010
The next step is to create a certificate request from the Exchange server. You can perform this task from the Exchange Management Shell, or from the console.
For an example of the Exchange Management Console steps see the previous article here.
From the Exchange Management Shell use the New-ExchangeCertificate cmdlet to generate a certificate request. In this example I am requesting a certificate with the following attributes:
- A friendly name of “Exchange 2010 Certificate”
- The server’s FQDN
- The alternative names of mail.exchangeserverpro.net, autodiscover.exchangeserverpro.net, and webmail.exchangeserverpro.net
I’m also using -GenerateRequest to create a certificate request rather than simply creating a self-signed certificate.
[PS] C:\>New-ExchangeCertificate -FriendlyName "Exchange 2010 Certificate" -IncludeServerFQDN -DomainName mail.exchangeserverpro.net,autodiscover.exchangeserverpro.net,webmail.exchangeserverpro.net -GenerateRequest -PrivateKeyExportable $true
The command will output a certificate request that looks similar to this.
-----BEGIN NEW CERTIFICATE REQUEST----- MIIEPDCCAyQCAQAwJTEjMCEGA1UEAwwabWFpbC5leGNoYW5nZXNlcnZlcnByby5u ZXQwggEiMA0GCSqGSIb3DQEBAQUAA4IBDwAwggEKAoIBAQCnbhSAM0y26udUo/+8 yvufXrv0AcuzcLYc/9wxNjgOZjmkQUqXEvrxXXrIzCciWL1KDTYjJyVXNkjqCsB3 8tdLWS7tLR/OLj0Px7bsUkTuJKl95DeYGJwxginMjvVKrdxMkPJloWY6i+5ZzHfs jhK0+bboyaoQMopwnya7AK0H5AfSDUd+hFzbgpX8hdj7hkMVwCS257/fsNkoJbxA xC7C9Yk06onHypefiz+uTubNULjKBKdtJiyesj6hakyG1tFddsvv6yqwjtAefyVZ vYWbkSJiXTwALuOrePlt3wGa12ZxqYwl2Mf98gdb2fTq2M6TosPE0PIxoDZvBzV2 IHZxAgMBAAGgggHQMBoGCisGAQQBgjcNAgMxDBYKNi4xLjc2MDAuMjBlBgkrBgEE AYI3FRQxWDBWAgEFDBtFWDMuZXhjaGFuZ2VzZXJ2ZXJwcm8ubG9jYWwMEEVYQ0hT RVJWUFJPXEVYMyQMIk1pY3Jvc29mdC5FeGNoYW5nZS5TZXJ2aWNlSG9zdC5leGUw cgYKKwYBBAGCNw0CAjFkMGICAQEeWgBNAGkAYwByAG8AcwBvAGYAdAAgAFIAUwBB ACAAUwBDAGgAYQBuAG4AZQBsACAAQwByAHkAcAB0AG8AZwByAGEAcABoAGkAYwAg /wQEAwIFoDCBhQYDVR0RBH4wfIIabWFpbC5leGNoYW5nZXNlcnZlcnByby5uZXSC ImF1dG9kaXNjb3Zlci5leGNoYW5nZXNlcnZlcnByby5uZXSCHXdlYm1haWwuZXhj aGFuZ2VzZXJ2ZXJwcm8ubmV0ghtFWDMuZXhjaGFuZ2VzZXJ2ZXJwcm8ubG9jYWww DAYDVR0TAQH/BAIwADAdBgNVHQ4EFgQUbaUvsgyyRXS0lEHebbnvEqpd7VwwDQYJ KoZIhvcNAQEFBQADggEBAEQ5GtxZGMf3rw+gGuIj+A8exB7bM2aSg9Z9X6RyNtHX 3iuCHPEOUdkZFSTR3CWoMal1FcH/r1yzCPXKTWDtyMIzi4tiHA/+V2nXALhH6Fbv c8G0l47iIGlbvuBkBDTxhmLubXgXGAp1dRfwRXd1Vqy0eDe/0LxlUAwq+Kb/RRLw UaUf3eVrbQUpWNqEmLcorp3mpwnoqAB+GhP+j0ERCquP629xdlHS2yz3fNfn4xGU Sv/i5FLUf6WmVJu+kjQ50wlh5nE+XiwQmsta0MNUnqIXu9dDXnOpx+VdmuKdEXlh /zAHMofanelZ/UUBv7mdwMG3E5U17nJ/VoiIAZAygg0= -----END NEW CERTIFICATE REQUEST-----
Copy the output to your clipboard for the next steps.
Open your web browser and navigate to the web enrollment URL of your Certificate Services server (eg http://ca-server/certsrv). Click on Request a Certificate. Note if you are running a Windows Server 2003 CA you may need an update to the web enrollment pages before you can proceed any further.
Choose Advanced Certificate Request.
Choose to Submit a Certificate request…, because we’ve already generated the request on the Exchange server earlier.
Paste the generated certificate request data into the form, and choose Web Server as the certificate template. Click Submit to continue.
Completing a Pending Certificate Request for Exchange Server 2010
The certificate has been issued and downloaded, and now the pending certificate request needs to be completed for Exchange Server 2010.
Launch the Exchange Management Console, navigate to Server Management, and choose the server that you imported the certificate to. Right-click the new certificate and choose Complete Pending Request.
Browse and select the certificate file that was downloaded, and the continue to complete the wizard.
The certificate has now been installed and is ready to be assigned to Exchange services.
If you encounter an error message stating that “The certificate is invalid for exchange server usage” then see this article for the solution.