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Self-Issued Security Certificate has expired on Windows SBS 2008

I came across this issue today with a client where all their Outlook clients were reporting that the server security certificate had expired.

Outlook errors with a notice of two out of three ticks like this image:

As mentioned, I found this to be the case with all clients in the organisation. Looking on the server it was all reporting the same thing (SBS Console > Network > Connectivity > Certificate > Properties )

To fix this issue:

  1. Logon on to your SBS Server.
  2. Open the SBS Console
  3. Go to Network > Connectivity tab
  4. On the right-hand side, click on “Fix My Network”
  5. Run through the wizard, and it will detect the expired certificate and issue a new one.
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