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We have a couple of vm servers still running Windows Server 2003 R2 Enterprise 32bit. There are many vulnerabilities and some of the ways of fixing the problem will be upgrading to a higher version of Windows Server and IIS. (Plus Microsoft stopped supporting Server 2003.)

I think we will have to go from 2003 to 2008, 2008 to 2012, and then 2012 to 2016? Is this the only way? or there are other better approach to upgrade to newer version?

And I guess data and configuration will need to re-do manually?

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    Why don't you just replace them? Why do you want to upgrade them? – joeqwerty Sep 8 '17 at 3:44
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    Agree, just do a migration of the server functionality over to the newly and freshly installed Windows Server OSes. I would not do all those OS in-place upgrades like that personally. Just get a new OS VM installed with Server 2016, start getting everything configured and tested from it and look over the production VMs until you get the migration environment tested, and then figure out what all you need to change for it to take over as production when you are ready (e.g. rename prod to old, rename migration to prod, make IP address changes, kick off copy scripts for data, etc.) just migrate. – Pimp Juice IT Sep 8 '17 at 4:17
  • @joeqwerty, I thought we can just clone the vm and upgrade it on the clone. Instead of replacing it. But I was wrong, it is not as simple as I thought it would be. And Replace is the way to go. – Nicholas Sep 8 '17 at 5:18
  • @MarijuanaTechnologyIT420, I see, thanks for all these information. I remember the previous system admin told me something similar before. I will have to gather all these information and send out an email to the team and see what they want to do, I will list out the risks and all the problem with 2003 (if we stay with 2003), and the amount of resources to replace it (If we are to replace to higher version) – Nicholas Sep 8 '17 at 5:33
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    You'll probably need a professional in order to get this job done. – Marco Sep 8 '17 at 13:22
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It's 32-bit. It can't be upgraded. Server 2008 R2 and newer only come in 64-bit versions. There is no upgrade path from 32-bit to 64-bit.

In addition, this would be like trying to upgrade Windows XP to Vista, to Win 7, to Win 8, to Win 10. I highly doubt you would attempt that on a home computer, so why consider it for a production server?

Instead, come up with a migration strategy that involves building out 1 or more 2016 servers and migrating domain roles, server roles, applications and files over.

You also need to consider replacing the hardware, as anything running server 2003 is beyond end of life and highly unlikely to support a newer OS very well if at all.

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  • I see. Thank you for the information. I will gather all the information and send an email out to the team for their opinion. I will try my best to research and learn more about Windows Server. new to this area. – Nicholas Sep 8 '17 at 5:49
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    Consider utilizing the services of a professional for this. – Appleoddity Sep 8 '17 at 17:33

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