SBS 2008 OWA says 404 file not found

What the problem is: OWA suddenly stops working after updates or a restart.

What is causing said problem: updates or a restart.

How to Fix SBS 2008 OWA 404 Error:

  • Log into the server and go into IIS 7 (the one that isn’t IIS6). Expand until you can see all the sites. The one called SBS Web Applications will be in the stopped position (you’ll see a little stop square on it).
  • Right click the Default Web Site and go to Edit Bindings. Remove the SSL 443 entry. This site isn’t even used for SBS but the SSL is applied to it for some reason and it causes this error.
  • Right click SBS Web Applications and go to Edit Bindings.  Double click on the 443 entry or create one for SSL 443 and assign the proper SSL certificate. If I did it, it should say cert2011 or something similar. Hit OK until you are back at the site listing. Right-click SBS Web Applications again and go to Manage Web Site  Start. Test OWA again and it should work.
  • If you can’t figure out which SSL Cert to use, there’s a couple ways to make a guess. In IIS7, click the server name and then click certificates on the right side to view them all. You can also go into the exchange shell as administrator and type ‘get-exchangecertificate’ to list them all with thumbprints. The one with the most letters assigned to it is probably the one to use.
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