Hello All,
I am planning to upgrade to 2012 r2 to 2019. Its a JDE Server and its a vm machine
Could you please help me to know the process like before start to upgrade. What all I have to take care.
like Backup ? etc.
See my guide... Before anyone tries to say don't do in-place upgrades.
https://www.ajtek.ca/wsus/another-successful-in-place-upgrade-why-not-change-how-you-think/
what's your thought ..Should we go with in place upgrade or newer OS on different server and migrate the application.
Any tool which we can run before in place upgrade to check system is healthy and ready for in place upgrade
Also one more thing.
Can we directly upgrade from 2012 r2 to 2019 or we have to upgrade 2016 then 2019.
the first option is grayed out from below printshot 
current OS on my server is
Name: Microsoft Windows Server 2012 R2 Standard
Version: 6.3.9600 N/A Build 9600
Very odd. I've upgraded from 2012R2 direct to 2019 in-place. Something like a Server Role or something is preventing the ability of in-place upgrading while keeping everything (example: RDS). Looks like you don't have a choice - you will have to build new and migrate.
As away of an analogy, you have a old jacket that you have had for a few year and its starting to wear a little thin and there are a few holes in the elbows, and there are a few stains here and there. You can try cleaning it and adding patches to cover the holes, but the holes are still there underneath and it still has the wear and tear as before. Or do you bite the bullet and buy a new jacket.
The same is true of a server, over the years it's had additional software installed, that may no longer be required, or some uninstalled but still has components left over, might be slowed due to the normal Windows bloat, and might have unknown security vulnerabilities. Yes it's possible to upgrade the servers, and if you don't have the software or configuration to be able to reinstalled this might be the only option, but all the previous issues and risk still exist. However, if you do have the software and configuration to reinstall, I would go with that option every time. You get a freshly installed OS with only the software that is required, and a known state. Its also the lowest risk option, as you still have the original server if something goes wrong.
Gary.
Ok in place upgrade what we have to verify on existing machine.
Like as I said in my test environment the first option is greyed out "Keep personal files and apps" Don't know why?
If I go https://docs.microsoft.com/en-us/windows-server/upgrade/upgrade-2012r2-to-2019 its pretty simple steps.
anything you guys recommend ..FYI, I have backup and its a VM machine.
Perform upgrade pre-checks
Perform upgrade staging steps
Perform upgrade process steps
Perform post upgrade actions steps
option is greyed out "Keep personal files and apps" Don't know why?
Most likely reason is using evaluation media. Evaluation media cannot be used to perform and in-place upgrade, you'll need to use licensed installation media. But an in-place upgrade is a risky move plus all of the corruption carry-forward. Always better to clean install the OS, patch fully, then do an orderly migration.
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Yes, I was also thinking license issue. but i had already applied license keys and it allow me for next action as well.
Regardless, evaluation media cannot be used for an in-place upgrade.
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As I said media is correct.
Sounds good, you can review the log files for further investigation.
https://docs.microsoft.com/en-us/troubleshoot/windows-client/deployment/windows-setup-log-file-locations
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