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As SQL Server 2005 end of life is getting closer I'm facing inevitable job of migrating databases, SSIS packages, SSRS reports and SSAS cubes. Since newest version of SQL Server is SQL Server 2014 we are probably need to switch to it. I have read few texts on migrating from SQL Server 2008 to SQL Server 2014 but i have not found anything about migrating from SQL Server 2005.

Have somebody else done something similar and can it be done in first place?

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There is no definitive answer to your question, since it will totally depend on the complexity of SSIS packages, SSRS reports and SSAS Cubes.

Doing in-place upgrade is always risky, since if something goes wrong, it would be difficult to rollback. A side-by-side migration is always a good and reliable method, since if something goes wrong, you already have a system up and running that you can point to.

Always, test, test and test your migration and have a fully tested rollback plan. Use upgrade advisor (this touches DB Engine, SSIS, SSRS and SSAS) and fully address all the issues raised by it.

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