In SQL Server 2005, Microsoft introduced the Upgrade Advisor. This was a great idea to be able to analyze your current SQL Server in a safe environment and start the planning process of an important upgrade. The key element of any Project Plan is Risk Management and this tool allowed you to prepare for an upgrade by assessing risk proactively, without introducing risk itself. You could then assess each issue that the tool identified on a case-by-case basis and start planning the upgrade project in a controlled strategic manner. The good news is that Microsoft has continued with this tool for SQL Server 2008. I have been testing the new version of the tool and wanted to discuss it here.
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