Wednesday, 10 October 2012

Self issued security certificate has expired, Windows SBS 2008


Windows Small Business Server 2008


Logged Warning Event ID: 64, certificate is about to expire.
Finally users are getting Security Alert pop-up in Outlook:
"The security certificate has expired or is not yet valid"


Two options:
1. Issue new certificate.
  • Logon on to your SBS Server.
  • Open the SBS Console
  • Go to Network > Connectivity tab
  • Switch back to SBS Console and on the right-hand side, click on "Fix My Network"
  • Run through the wizard, and it will detect the expired certificate and issue a new one.
Now you may need to Export that certificate and import it on every client connecting to the server.
  • In SBS Console right click "Certificate" and select "View certificate properties"
  • Make sure there is no errors or warnings in here
  • Close certificate pop up window
  • Now click "Open Certificate Installation Package", which will open "C:\Users\Public\Downloads"
  • You will find here "Install Certificate" which contains InstallCertificate.exe and SBSCertificate.cer
  • Copy that zip to every pc and double click InstallCertificate.exe, which will inject it into "Trusted Root Certification Authorities" store.
  • Use Group Policy to automate it:
  • "Computer Configuration > Policies > Windows Settings > Security Settings > Public Key Policies/Trusted Root Certification Authorities"
  • Import SBSCertificate.cer file
  • Give it at least 90 minutes to propagate
2. Renew certificate with the same key, it does not enhance the security
  • Logon on to your SBS Server.
  •  Start > mmc
  • Add Certificates (Local Computer)
  • Go to Personal > Certificates and find your expired certificate
  • Right click on it and select All Tasks > Advanced Operations > Renew this certificate with the same key
 I haven't tested second option, but assume it should work.


  1. EXCELLENT EXCELLENT EXCELLENT Tutorial! Keep up the good work!

  2. Have to hit you up again, EXCELLENT EXCELLENT EXCELLENT Tutorial! Keep up the good work!

    This was a huge issue and there are 12 users.

  3. I am very pleased that it worked for you! :)