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Should I be scared of upgrading the database to SQL Server 2008?
Is it a simple auto-upgrade and everything works?
Is it worth it?

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The upgrade from SQL Server 2005 to 2008 is a lot less "scary" than the upgrade from SQL Server 2000 to 2005. There are fewer T-SQL enhancements this time around, and the tools to manage SQL Server are very similar (so less of a learning curve).

The one thing that most people forget to do is to change the compatibility level of their databases after the server has been upgraded; you need to do this in order to use the new features inside a particular database after the server has been upgraded.

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