WTF SBS? Re-running the Connect to the Internet wizard (see last post) apparently resets a web.config file, breaking the SSO features between RWW and OWA.
The link above applies to EBS but is also applicable to SBS as well (instead of hitting the "c:\program files\Windows Essential Business Server\Bin\webapp\Remote" folder use the "c:\program files\Windows Small Business Server\Bin\webapp\Remote" folder instead).
Changing "Sites" to "remote.blahblah.com" in the right place inside the web.config file mentioned above will sort out the issue.
Note that this may only be a problem when you need a very specific hostname configuration due to certificates, Outlook Anywhere, etc. It's unlikely this will be a problem on a vanilla SBS 2008 without much customization.
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4 hours ago