Resolved via Microsoft.
There are apparently issues with SSL connectivity and basic installs of SQL Server 2008. After installing “SQL Server 2008 Service Pack 3” and following it up with “Cumulative Update 6” (and rebooting) the SSL connection succeeded.
General notes for anyone wanting to do this in the future:
- For testing purposes a self signed certificate works if you add “trustServerCertificate=true” to the client connection string
- UPDATE your SQL server with MS patches
- Aside from selecting the Certificate and setting the “Force Encryption” setting to yes, no further configuration is needed within SQL Server Configuration Manager