From the Department of I Wish The Prerequisite Analysis Checked for This, comes the unfortunate issue that customers with expired SSL certificates will run into when they try to install an Exchange cumulative update. In short, the CU install will fail, and the server will be left in a broken, non-functional state.
During the cumulative update the following error will be thrown:
Mailbox role: Transport service FAILED
The following error was generated when “$error.Clear();
Install-ExchangeCertificate -services IIS -DomainController $RoleDomainController
if ($RoleIsDatacenter -ne $true -And $RoleIsPartnerHosted -ne $true)
Install-AuthCertificate -DomainController $RoleDomainController
” was run: “System.Security.Cryptography.CryptographicException: The certificate is expired.
at Microsoft.Exchange.Configuration.Tasks.Task.ThrowError(Exception exception
, ErrorCategory errorCategory, Object target, String helpUrl)
at Microsoft.Exchange.Configuration.Tasks.Task.WriteError(Exception exception
, ErrorCategory category, Object target)
at Microsoft.Exchange.Configuration.Tasks.Task.InvokeRetryableFunc(String fun
cName, Action func, Boolean terminatePipelineIfFailed)”.
This isn't so much a flaw in the Exchange setup process as it is a stark reminder of just how common it is to see poorly maintained servers in the field. Imagine all the Exchange servers that aren't being backed up at all (and there's plenty of those out there), creeping ever closer to filling up their transaction log drive and dismounting databases. Viewed through that lens it's easy to also picture an office full of staff dutifully clicking past the expired certificate warnings they see in Outlook and their web browser every day to get to their email. It's almost ironic that after neglecting a server to the point where its cert has expired, that when the admin finally tries to do some maintenance by installing a CU they're going to end up making things worse.
Anyway, once you've found yourself in this hole, you're going to need a quick way out. Looking around for solutions you might find your way to the instructions for renewing an Exchange certificate. Your bad day doesn't get better yet though, because you discover that you can't connect to any of the Exchange management tools for your server.
But all is not lost! Fortunately, you can manage the certificate bindings using IIS Manager on the Exchange server. Select the Default Web Site, click the Bindings link in the Actions pane, and edit the bindings for HTTPS (there should be two of them for port 443, and you'll need to do both). From the list of SSL certificates, you should see one called “Microsoft Exchange” that is the self-signed certificate that was automatically configured on the server when Exchange was installed. Just to be sure, click on View and check whether it's expired (it should have a 5 year lifespan).
Apply that change and re-run the Exchange cumulative update.
If for some reason the self-signed certificate doesn't work, or is missing, you can generate a new one in IIS Manager by clicking on your server, opening the Server Certificates section, and selecting Create Self-Signed Certificate.
When you've successfully completed the cumulative update for your Exchange server, it's time to do something about your certificate problems. There'll be a cost involved, usually not more than a few hundred dollars, which hopefully by now you consider a bargain. Here's some reading for you: