Since it's ridiculously easy to stand up a server I see no reason to do an
inplace upgrade ever[1].

Assuming your licensing is in shape, stand up a new VM, get it ready,
transition services, and then decommission the old VM.

[1] Licensing is the issue in this matter, if you're out of licenses
standing up a VM may not be possible.  Another point in favor of Datacenter
Edition.
2011/10/4 Paul Hutchings <[email protected]>

>  I haven't upgraded a Windows Server install for years now as typically
> with physical boxes the box gets replaced after a three year period so the
> OS is rebuilt/refreshed.
>
>  Virtualisation has changed that somewhat as we now have VM's with a
> potentially infinite "physical" life, and as a result I have quite a few
> that are still running Windows 2003.
>
>  I may rebuild them all with 2008 R2 which also solves the fact that right
> now they're 32bit, but what are peoples experiences of upgrading Windows
> in-place?
>
>  As I said I've not had to do so for years now so I'm out of touch with
> how good/bad of an experience it is these days? The one potentially nice
> thing is that other than any third-party apps, the VM's are about as clean
> as you can get, no HP PSP or suchlike to have to deal with.
>
>  I should add we're talking small role-specific VM's here, nothing crazy
> like Exchange.
>
>  Thanks,
> Paul
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