In place Upgrade from Win 2008 to 2012

Check if any applications are installed are compatible with 2012 R2.

I would also backup the VMs, because upgrades do fail.

I've not seen any 2012 or later ISOs, slipstreamed....you would have to check.

If these are just file servers, just create new servers and transfer data and shares.

Thanks Andrew,

Applications are verified no issue with applications

Major problem here is Disk Size /block size limitation failing to add more space after 16TB Disk

Creating new VM and moving Data will not be more pain moving Files and Permissions/Shares  ?

Backup is fine as it may fail too

Ultimately you need to decide 1st which OS you want to GO and what licenses you have in hand

2008 R2 can be in place upgraded to 2012 R2

From 2012 r2 it can be further upgraded to 2016 / 2019

Note that some services won't allow you to make in place upgrade like AD certificate services

Domain controllers can be in place upgraded as long s you extend schema in advance

File servers should not face any issues for in place upgrades

https://docs.microsoft.com/en-us/windows-server/get-started/installation-and-upgrade
https://docs.microsoft.com/en-us/windows-server/get-started-19/install-upgrade-migrate-19

Easy to move files and shares...and a lot less painfull.

1. Use Robocopy to sync the data.

2. Export the Registry for the Shares.

Done.

(later if you wish you could rename and re-add the new server back to original)

Thanks Andrew, any way to automate the same for multiple boxes?

Thanks Mahesh,no doubt about os n licencing here,only query is to upgrade max with min manual interventions

You could script it, but to be honest with you the time taken to develop the scripts, could be time taken to manually do the upgrades.

@Mahesh

How does robocopy automate the VM Upgrade process from Windows 2008 R2 to Windows 2012 R2 Server ?

I believe this is the question being asked....

@Andrew - Thanks for the help here. Please help to chose the best practice here like if we only have File Server

Here are plans if that will work

We can have customized ISO for 2012 with help of Sysprep ,Capture and then will use Oscdimg.ex ?

What if we simply create new VM using template  and then will map old disk from old VM[old VM need to be powered off/renamed during this activity] to new VM and simply enable share for folder as it was earlier on old VM ?
Can we use the same approach from 2003 to 2008 then for 2019 ? , as our final destination is 2019
What all are precautions required for a VM Upgrade or only Snapshot is fine to revert back in case issues ?

@Mahesh - Thanks for your valuable suggestions

 Regarding  Robocopy what if we have huge size Disk like in 16+TB and more
 and what should be approach for physical Box

What if we simply create new VM using template  and then will map old disk from old VM[old VM need to be powered off/renamed during this activity] to new VM and simply enable share for folder as it was earlier on old VM ?
Can we use the same approach from 2003 to 2008 then for 2019 ? , as our final destination is 2019
What all are precautions required for a VM Upgrade or only Snapshot is fine to revert back in case issues ?

Create a new virtual machine with server 2019.

If all the data is on an existing disk on the old VM, just remove the disk from that VM and attach to the new, and Import the shares.

(it's done!).

Shutdown the old machine, and rename the new machine, give the same IP and your done.

Great Thanks.

so it is just to enable Share manually like it was on old VM or if some other automated process?

Export and Import the share information, or re-create them manually.

Approach is fine but what if we have spanned volume used for VM disk ? can we map the same to new VM?

As long as you add in the same order, spanned disks are not recommended and bad practice, I would clone the spanned volume to a single disk.

Great Thanks!!

Will try it for File Server

Created customized ISO for 2012 with latest Patches but after upgrade  result vm is coming out of domain? should not be any issue ?

What should be valid approach for Print Server and AD DC/CDC with FSMO and VC already ruining on windows 2008 Std

Can we go with in place upgrade for DC,CDC ,Print Server and VC?

You will find it's not supported and in-place upgrade will break stuff!

Really but Why ? is it not supported in 2012?

vCenter Server!

upgrade not supported and VC will break!

Okay,

There is one Feature available in 2019 ie Storage Migration Service -hope that will be great help here to migrate my 2003 File Server to 2019 but not others ?

Not sure if it will work as fast as we copy data/disk using robocopy ?

No, Migrate from the existing 2019 server.

2019 is actually experiment for me but will try,Thanks

Great Help by Mahesh and Andrew here

I have prepared customized iso and helped a lot to save more time here