Upgrading windows server 2003 to 2016

Question

I wish to upgrade my windows server 2003 to windows server 2016, is there any easy procedure to do that? The 2003 server contains an application so is there any way doing it without data loss?
Are there any other things I have to be informed about while doing it?

thanks.

Answer 1

In addition to the mentioned fact that there is no direct upgrade path, the fact that you have a custom application running under IIS adds another level of major complexity. There have been very significant changes made to IIS since 2003. You need to test that application on 2016 IIS before you even think about attempting to upgrade. So why not start at the beginning to reach the end? Build a 2016 system and install the application to see if it even runs on 2016.

Answer 2

Do not do an in-place upgrade. There is no direct upgrade path, it would need to be a multi-step process. The hardware is also unlikely to be supported for such a change. You can check here and also with manufacturer about support for the hardware.
https://www.windowsservercatalog.com/

https://learn.microsoft.com/en-us/windows-server/get-started/supported-upgrade-paths#upgrading-previous-retail-versions-of-windows-server-to-windows-server-2016

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Answer 3

Hi,

There is no direct upgrade path from Windows Server 2003 to Windows Server 2016.

You can use the following diagram to figure out which Windows Server version you can upgrade to, based on the version you're currently on:

However, the important point is that there is no upgrade path from 32-bit to 64-bit, and Windows Server 2016 is only available in 64-bit.
Instead, you should concentrate on migrating services. The alternative would be backing up the application and role states to a file, performing a clean installation of Server 2016, then restoring the application and role states,
Windows Server Migration 2003 to 2016
https://techencyclopedia.wordpress.com/2017/02/02/windows-server-migration-2003-to-2016/
Please note: Information posted in the given link is hosted by a third party. Microsoft does not guarantee the accuracy and effectiveness of information.

It is generally recommended to perform an fresh install rather than an upgrade, at least if this is a domain controller.

For your reference:
https://learn.microsoft.com/en-us/windows-server/get-started/installation-and-upgrade

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Answer 4

There is no direct upgrade path, it would need to be a multi-step process.
https://learn.microsoft.com/en-us/windows-server/get-started/installation-and-upgrade

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