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answers:

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There was a similar thread on this earlier, but my question is specific to upgrading from SQL2005 to 2008: when upgrading in-place is not possible because the machine has to be re-imaged, which method is preferrable - detaching and re-attaching the db files, or backup/restore?

Detach/attach is obviously faster and accoding to msdn possible, but I wonder if anyone could share real life experiences?

Thanks Max

+1  A: 

Backup/restore would be the recommended method.
Reason being, if something goes wrong you always have the unaltered original (and a copy of the backup if you had the foresight) that you can go back to. You don't have that option if you use detach/attach.

OMG Ponies
true, but if your copying to another box over the network, you'll have the files still in the original location. Just don't do a move!
Nick Kavadias
A: 

how much down-time is allowed for your cut-over:

How big are the databases that need to be copied?

backup/restore + logshipping may be the fastest way to do a cut-over if time is critical. With either detach/attach or backup/restore the longest part is waiting for the file copy to finish.

Nick Kavadias