Suggestions for moving datastore?

I have a disk on a Windows Server 2003 virtual machine that is 500GB and is essentially just a drive that contains a folder that is a share (through the Windows 2003 file share role).
This folder is also mounted within vSphere (v 5.5, esxi hosts) as a Datastore for all the hosts.

Since I'm trying to retire the Windows 2003 servers, what's the best thing to do with this disk to maintain its accessibility for the select users that access its files?

I understand I will need to detach the disk from the Windows 2003 server (but keep it in the datastore). But should I then just simply attach the disk to, say, a Windows 2012 R2 server? Will it maintain its file-sharing permissions for the folder that's on it, or go wonky within Windows 2012 (be it with permissions or disk initialization, etc, since it's coming from Windows 2003).
garryshapeAsked:
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Lee W, MVPTechnology and Business Process AdvisorCommented:
What happens depends on how your network is setup.

If it's a Windows Domain, then the SIDs are domain based so the NTFS security should be preserved just fine.  If it's a workgroup, then none of the NTFS security will apply - you'll lose it all.

In either case, SHARE permissions (as opposed to NTFS permissions) will be lost.  However, *IF* you mount it as a the same drive letter on the new server, you can simply export the lanmanServer service registry key and re-import and that should preserve the shares and share permissions. (I wouldn't bother with this if you only have a couple or share or so... and share permissions are, in my opinion, mostly pointless - you should rely on NTFS permissions anyway, so that too should be on the pointless side).
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
I understand I will need to detach the disk from the Windows 2003 server (but keep it in the datastore). But should I then just simply attach the disk to, say, a Windows 2012 R2 server? Will it maintain its file-sharing permissions for the folder that's on it, or go wonky within Windows 2012 (be it with permissions or disk initialization, etc, since it's coming from Windows 2003).

It will retain the NTFS permissions on the disk, but you will need to reconfigure the Share Permissions in the new OS. It's a simple process, and many are doing this migration method.
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garryshapeAuthor Commented:
Ok great guys, thanks
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garryshapeAuthor Commented:
Actually got a follow-up question on same topic.
Could I just upgrade the 2003 server to 2008 R2? It'd keep the D-Drive intact with the files being shared? It is NTFS, and only sharing to one AD security group.
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
if its on the supported upgrade path - yes inplace upgrade can work.
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Lee W, MVPTechnology and Business Process AdvisorCommented:
No.  Well MAYBE.  2008 R2 is a 64 bit only system.  If your Windows install is 32 bit, then no.  There is, has never been, and likely will never be, a supported upgrade path from ANY 32 bit system to a 64 bit system.

That said, if it is 64 bit I would still say DON'T DO IT, even if it's supported.  ESPECIALLY on servers, it's far better (CLEANER, less risk of issues, strange and otherwise, creeping up) to do a clean install and migrate data.
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garryshapeAuthor Commented:
yep, that was the case, lol -- 32 bit, couldn't upgrade.
grrrr.... Oh well, I'm fine that I acquired it. always up to the challenge.
The solution still stands but the predicament currently is sorting out my datastore issues. lol
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