This is a bit outside of my domain - Reporing Services may be able to help faster (forum: http://forums.microsoft.com/MSDN/ShowForum.aspx?ForumID=82&SiteID=1)
One thing you could try is setting the ReportServerUrl to the fully-qualified domain name of the server for which your SSL certificate was issued. From
http://msdn2.microsoft.com/en-us/library/ms159261.aspx
"If a Secure Sockets Layer (SSL) certificate is installed, this value must be the name of the server that is registered for that certificate. If you get the error "The underlying connection was closed: Could not establish trust relationship for the SSL/TLS secure channel", set ReportServerUrl to the fully-qualified domain name of the server for which the SSL certificate was issued. For example, if the certificate is registered to https://adventure-works.com.onlinesales, the report server URL would be https://adventure-works.com.onlinesales/reportserver. "
Let me know if this helps.
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