PrivateKeyMissing when running Enable-ExchangeCertificate

PrivateKeyMissing when running Enable-ExchangeCertificate

Enable-ExchangeCertificate : The certificate with thumbprint XXXXXXXXX was found but is not valid for use with Exchange Server
(reason: PrivateKeyMissing).
At line:1 char:27
+ Enable-ExchangeCertificate <<<< -Thumbprint XXXXXXXXX -Services "IIS"

The above error is a result of a glitch with Exchange 2007. This issue does not happen all the time as it is completely random, but when it does happen no certificate can be installed or removed through the Exchange Management Shell (EMS). For whatever reason it may be, the system forgets where it placed the Private Key or the certificate store is damaged.

Repair Damaged Certificate Store:

1) Open MMC (Microsoft Management Console) to the Certificate Manager (Certificates Snap-in) for the Local Computer account.
2) Double-Click on the recently imported certificate (It will be missing the golden key).
3) Go to the Details tab.
4) Click on the Serial Number field and copy down that number. (Leave window open)
5) Open up the command prompt (DOS Prompt -- CMD.exe)
6) Type: certutil -repairstore my "SerialNumber"( SerialNumber is that what was copied down in step 4.)
7) After running the command, go back to the MMC and right-click Certificates and select "Refresh".
8) One should now see the golden key associated with the certificate.
9) Double-check in the Exchange Power Shell with: Get-ExchangeCertificate

Alternatively if the above does not work try the following:
Note: Follow these steps if running Windows Server 2008 only

1) Open MMC (Microsoft Management Console) to the Certificate Manager for the Local Computer account. (Certificates Snap In)
2) Look in the Personal section of the Certificate Manager and there should be icon(s) without a little golden key. (Those with the key have the private key bonded to them.)
3) Delete the icons without the golden key.
4) Go back to the EMS.
5) Run the Import-ExchangeCertificate and Enable-ExchangeCertificate in one line like so: [ Import-ExchangeCertificate -Path c:\exchange.globessl.com.crt | Enable-ExchangeCertificate -Services "SMTP, IMAP, IIS, POP" ]
*** Please modify the command according to your needs. ***
6) Things should be golden from here and if they are not, please contact Microsoft.

Renewing the Self-Signed Certificate: Exchange Server 2007

This is another perfectly written article that I have borrowed on this subject.  I got it from Exchangepedia and the author Bharat Suneja deserves all the credit.

Exchange Server 2007 issues itself a self-signed certificate for use with services like SMTP, IMAP, POP, IIS and UM. The certificate is issued for a period of one year.

The self-signed certificate meets an important need – securing communication paths for Exchange services by default. Nevertheless, one should treat these certificates as temporary. Although the self-signed certificates work perfectly well for internal SMTP communication between Hub Transport servers, and between Hub Transport and Edge Transport servers, it’s not recommended to use them for any client communication on an ongoing basis. For most deployments, you will end up procuring a certificate from a trusted 3rd-party CA (or perhaps an internal CA in organizations with PKI deployed).

Should you decide to leave the self-signed certificate(s) on some servers and continue to use them, these will need to be renewed when they expire — just as you would renew certificates from 3rd-party or in-house CAs.

 1. To renew the certificate for server e12postcard.e12labs.com, a server with CAS and HT roles installed:

Get-ExchangeCertificate -domain “e12postcard.e12labs.com” | fl

Note the services the certificate is enabled for (by default: POP, IMAP, IIS, SMTP on CAS + HT servers). Copy the thumbprint of the certificate.

Get a new certificate with a new expiration date:

Get-ExchangeCertificate -thumbprint “C5DD5B60949267AD624618D8492C4C5281FDD10F” | New-ExchangeCertificate

To create a new certificate with an exportable private key, use the PrivateKeyExportable parameter. For example:
New-ExchangeCertificate -PrivateKeyExportable $true

If the existing certificate is being used as the default SMTP certificate, you will get the following prompt. The default SMTP certificate is used to encrypt SMTP sessions between transport servers in your organization.

Confirm
Overwrite existing default SMTP certificate,
‘C5DD5B60949267AD624618D8492C4C5281FDD10F’ (expires 8/22/2008 7:20:34 AM), with certificate ’3DA55740509DBA19D1A43A9C7161ED2D0B3B9E3E’ (expires 1/28/2009 7:37:31 AM)?
[Y] Yes [A] Yes to All [N] No [L] No to All [S] Suspend [?] Help
(default is “Y”):

Type y to continue. A new certificate is generated.

Thumbprint   Services   Subject
———-   ——–   ——-
3DA55740509DBA19D1A43A9C7161ED2D0B3B9E3E   …..   CN=E12Postcard

The new certificate is generated and enabled. Examine the new certificate:

Get-ExchangeCertificate -thumbprint “3DA55740509DBA19D1A43A9C7161ED2D0B3B9E3E” | fl

2. The old certificate is enabled for IIS, POP, IMAP and SMTP. The new certificate generated using the above command is enabled only for POP, IMAP and SMTP – IIS is missing.

You can enable the certificate for IIS (in addition to any other services it may already be enabled for — it adds to existing values of the certificate’s Services property).

Note: Once you enable a certificate for a particular Exchange Server service, there’s no way to disable it (for that service). You must remove the certificate (if the certificate is CA-issued, export the certificate along with its private key before you do so), import it again and enable it for the services you need to. This is generally not a concern with self-signed certificates— you can generate additional self-signed certificates and optionally remove the old one, since there’s no CA interaction or costs involved.

Setting the Services parameter to None does not do anything in this case.

To enable the certificate for IIS:

Enable-ExchangeCertificate -thumbprint “3DA55740509DBA19D1A43A9C7161ED2D0B3B9E3E” -services IIS

3. Test services are working with the new certificate. If it works as expected, the old certificate can be removed:

Remove-ExchangeCertificate -thumbprint “C5DD5B60949267AD624618D8492C4C5281FDD10F”

Active directory response: 00002098: SecErr: DSID-03150BB9, problem 4003 (INSUFF_ACCESS_RIGHTS)

Active directory response: 00002098: SecErr: DSID-03150BB9, problem 4003 (INSUFF_ACCESS_RIGHTS)

If you're getting this error trying to move mailboxes from Exchange 2003 or 2007 to Exchange 2010 then here's the simple fix.

• Go into the user's account in AD and go to the Security tab. 
• Check the box to Inherit permissions. If it's already set, clear it, force an AD update, and then check the box again. 

I had 2 boxes do this on my last Exchange migration. It's a real pain to find out after you've waited on the mailbox to copy but a very easy fix.