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I need to upgrade some VMs due to the EOL of 2003. Many VMs can just be replaced with current version, but some are so old that it is easier to just try an upgrade and fallback if it doesn't work. There are two groups:

  • Windows 2003SP2/R2 (32-bit) to Windows 2008 SP2 (32-bit)
  • Windows 2003Sp2/R2 (64-bit) to Windows 2008 R2 SP1 (64-bit)

I've tested this process on a few VMs manually with success, but installing all current patches adds a lot of time to process. I would like to create upgrade sources that contains all (or at least most) current patches. I have volume media that integrates the most recent service pack to start from. I've done something similar long ago using DISM. Does anyone know of a step-by-step guide/resource to performing creating such a source?

InfoJanitor
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  • Why are you upgrading to a 5 year old operating system? – MDMarra Feb 03 '15 at 23:13
  • Could be for ease of upgrade (is there a direct 2003-2012 path?), could be for familiarity of interface/training for users, could be for licensing ("We have 6000 RDS CALs for 2008. No, you can't install 2012."), could be for software compatibility. It's not like 2008 is going to disappear tomorrow or even in the next 4 years (though I would recommend trying to get those 32-bit systems migrated to 64-bit). – fencepost Feb 04 '15 at 05:38
  • For 2008SP2--applications using IE8 published thru Citrix. For 2008R2 applications requiring a 16-bit subsystem For both -- applications not certified on 2012+ There is no direct 2003 -> 2012+ upgrade path – InfoJanitor Feb 04 '15 at 23:18

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Two options turned up for me that include support for server operating systems:

I've not used either, so I can't vouch for the usability of them - if you try, perhaps update in a comment?

Other options such as AutoPatcher seem to be for the client/desktop OSes only.

fencepost
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  • Investigating WSUS Offline. Found [Article](http://www.sysadminlab.net/mobile/creating-a-fully-patch-install-wim-for-windows-78-without-mdt-but-using-wsus-offline-updater). Will try that out. Thanks for the pointer. – InfoJanitor Feb 04 '15 at 23:21