How To: GoDaddy SSL Problems on Small Buisness Server 2008

My customer has a 2003 Small Business Server environment that has been in production for five years. Every application offered in the SBS 2003 package is being used. Because the customer is using multiple friendly addresses from the outside to connect to there Share Point, Web Mail access, FTP and a custom web app. They purchased a wild card SSL from GoDaddy to make it easier and use one SSL certificate. The wild card *.mydomainname.com allows them to provide one SSL for all the friendly names each website application needs. The customer decides to migrate to Small Business Server 2008 with the newer versions of Exchange, IIS and SharePoint.

Microsoft provides a migration path from SBS 2003 to SBS 2008 that takes longer then building a new network from scratch for this company. After all the applications are migrated and working the old SSL is imported onto the new server. The company begins to have problems connecting to the apps from the outside or allowing Internet access to them. The access is configured as recommended by Microsoft using the SBS wizard but fails shortly after a server reboot or restarting the IIS services. There are no event log notices or issues while connecting inside the network. I'm using the same SSL purchased for the SBS 2003 server apps but exported and imported for the new server. I take a chance and purchase a new SSL certificate for our email web access only webmail.mydomainname.com.

My Webmail problems go away but I still have SharePoint and FTP issues. Turns out the SBS 2008 does not like using not only a GoDaddy certificate but especially a wild card GoDaddy SSL certificate. So a purchase of a new certificate for each friendly address was needed to allow access to the apps from the IIS server without a timely shutdown. Here is a link I found while researching the issue.
http://sbs.seandaniel.com/2009/02/installing-godaddy-standard-ssl.html