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upgrading Operating system

we are in the planning phase of upgrading the operating system on all the servers in a citrix server farm from windows server 2003 std sp1 to windows 2003 ent R2 sp2. we will be upgrading the MS hotfixes and citrix hotfixes. JRE will be updated. The issue is we have a lot of applications published in the farm and there is no way we could install all these applications on the thest servers and test them for upgrade. My question is are there any precautions i need to take or things i need to thoroughly look into before in the planning and implementation process. any means of rollback if any application misbehaves. need some suggestions form the experts

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mgmohiuddin
Asked:
mgmohiuddin
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Malli BoppeCommented:
Just upgrade one server make an image of it.put it in production for 2-3 weeks see if any one complains.if every thing goes fine then use the image to install it to the other servers.
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Robin CMSenior Security and Infrastructure EngineerCommented:
if you have a virtual host of some description then this is ideal for this kind of testing and can save you loads of time.
Most vendors have a free offering and are pretty good if you have an reasonable spec box to run it on. You can P2V (physical to virtual) one of your live servers, snapshot it and then run the upgrade over and over again just reverting back to the snapshot each time you have an issue. Much quicker than ghosting your physical server and having to wait for it to ghost back each time. Won't help with testing possible physical server device driver issues though, as the virtual drivers are different. But if you're kepping the OS version the same (e.g. 2003 32-bit) this shouldn't be a problem anyway).

Bear in mind that to change OS from 2003 standard to 2003 enterprise you have to reinstall - it's not an upgrade (unlike changing the version of Vista).
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Carl WebsterCommented:
I disagree with you robincm, upgrading the OS from Standard to Enterprise is NOT a reinstall.  I have done this numerous times on Terminal Servers, Citrix Servers and Exchange Servers.  You will need to reapply ALL Microsoft updates.  Other than that there should be no issues.

BACKUP or IMAGE FIRST!!!!!

Do ONE server, test for a good while and then do the rest.
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Robin CMSenior Security and Infrastructure EngineerCommented:
I stand corrected :-)

And for anyone else who thought the same as me, here's the proof:
http://technet.microsoft.com/en-us/library/cc737287(WS.10).aspx
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