windows installation with RDP

MrJ

I've got a dedicated server with two ssd disks with windows server 2008 r2 and i want to upgrade it to server 2016 but i have only rdp access to the server. I tried creating a unattended answer file to install the OS but it gives a error when creating the catalog file is there any workaround to upgrade my server to windows 2016 btw i bought it from wholesaleinternet they only offer windows 2008, centos 7, rescue disc, 3 versions of ubuntu, proxmox, vmware esx, and debain

fernandosm

I would say you don't have many choices without a KVM as part of the process will happen offline and you will not be able to connect. The only "workaround" you can try is to create an image of the os disk (or the virtual disk if you are using any type of RAID) and virtualize it "at home", do the upgrade and then use DD or any imaging software that you can run from the recovery environments available to write the image back to the dedicated server.
you may have lots of different isses like OS crashing because of different HW used, your dedicated server's recovery environment not being able to correctly write the image to disks, etc.
It all depends on how far you want to go with the risks but I would say the chances of having a risk-free experience are 0% :-)

feezioxiii

boot into rescue and follow: windowstemplate.com

solaire

@fernandosm said:
I would say you don't have many choices without a KVM as part of the process will happen offline and you will not be able to connect. The only "workaround" you can try is to create an image of the os disk (or the virtual disk if you are using any type of RAID) and virtualize it "at home", do the upgrade and then use DD or any imaging software that you can run from the recovery environments available to write the image back to the dedicated server.
you may have lots of different isses like OS crashing because of different HW used, your dedicated server's recovery environment not being able to correctly write the image to disks, etc.
It all depends on how far you want to go with the risks but I would say the chances of having a risk-free experience are 0% :-)

You can actually fully automate a Windows installation, if I'm not mistaken it's called unattended install. NTLite might be worth looking into, though Microsoft supplies a tool that can do the same, but I cannot think of the name right now.

WSS

@solaire said:
You can actually fully automate a Windows installation, if I'm not mistaken it's called slipstreaming. NTLite might be worth looking into, though Microsoft supplies a tool that can do the same, but I cannot think of the name right now.

Windows PE?

solaire

@WSS said:
Windows PE?

Yep! Lots of things have changed over the last couple of years, but Windows ADK / Windows PE definitely looks like what I have been working with a couple years ago.

@MrJ
https://docs.microsoft.com/en-us/windows-hardware/get-started/adk-install
https://www.derekseaman.com/2012/07/windows-server-2012-unattended.html (pretty sure it'll work with Server 2016 too, though you might need a different version of Windows ADK)