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I have a SQL 2005 Std edition server with 5 databases in production, 4 db's are used by web-based apps the 5th is a desktop application. My question is should I perform an in-place upgrade or a side-by-side by creating an sql2008 instance on the same box?

The machine is a VM on vmware and I'm planning on taking a snapshot before the upgrade and having a 'blackout' window during the upgrade so that I could roll back to the snapshot if things go really bad.

Any previous experience and advice is appreciated.

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up vote 1 down vote accepted

since it's a VM I'd clone it, give the clone another IP and do an inplace upgrade. If all goes well inplace upgrade the production machine. Snapshots with databases sometimes don't work as expected. You also have the abilty to test during normal hours.

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I ran an in-place upgrade on my dev box and had no issues at all. I think with your snapshot as a safety net, you should be just fine.

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