A Guide to Troubleshooting Outlook Certificate Warnings/Authentication Prompts in SBS 2008 – The Official SBS Blog – Site Home – TechNet Blogs:
http://blogs.technet.com/b/sbs/archive/2010/08/19/a-guide-to-troubleshooting-outlook-certificate-warnings-authentication-prompts-in-sbs-2008.aspx?

Normally when you see “I’m getting prompts from Outlook” and we knee jerk say to install rollup 8 or later or SP3.   But you can see from that blog post there are lots more reasons for it.

 

 

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