Thanks for taking the time to read this. I am looking for your opinion or advice on the subject.

We have a physical server that is our DC, running AD, DNS, DHCP, and is also the file server. The file server alone takes up 1TB of space. This server is running Server 2008R2, so after the conversion it would need to be upgraded to 2012R2 and then 2016/2019.

I am looking to move this to virtual, and wondering the best process. Does it make more sense to try and convert this using the VMWare converting tool and upgrading the OS afterwards? OR do I just spin up a new VM running Server 2016/2019 and start from scratch?

Concerns: If I convert the server using the tool, I'm afraid it will take up a ton of space, which I might not have enough free space to even do this, and I'm concerned about how long the conversion will take. During this process if someone saves files or modifies files on the server, they will not be in the VM, right? If I spin up a new server, I'd have to copy everything over, but I'm concerned about getting the new server ready and prepared without conflicting with the old one. Things like DHCP, and AD. I would need the new server to be the same server name and same IP as the old server so that my devices know where to check in for DNS, DHCP, AD etc.

What advice opinions does the community have on the best way to do this.

Thank you in advanced!!

  • 2
    Tools like that should not be used on a domain controller. A far better option would be to setup a new domain controller on the virtual server guest, and demote the domain controller on the existing 2008 R2 server. – Greg Askew Aug 20 '19 at 17:10

I would need the new server to be the same server name and same IP as the old server so that my devices know where to check in for DNS, DHCP, AD etc.

Not required. You can deploy another AD DS + DHCP + DNS host with a new name and new IP. Reduces the chance of conflicts and makes the revert plan easier.

  • All DCs are in a group and in DNS.
  • DHCP responds to broadcasts, IP is less important. Because it is broadcast, only run one at a time; shut down old DHCP before starting new.
  • DNS server IP could be tricky. Run both while advertising the new one with domain policy, DHCP options, and reconfiguring static hosts.

Demote old server when the new one is working.

The ease of adding a new DC makes P2V style conversion plus upgrade unnecessary. New installs are safer and cleaner.

  • or keep the old running until you got a snother dc, its almost a good Thing to have atleast two dc – djdomi Aug 21 '19 at 4:47

If you still have 2008R2, the hardware might be rather old, too, and possibly not ideal for virtualization. If there's any chance to get a new server, I'd recommend installing a new Windows Server 2016/2019 as the Hyper-V host.

The problem with both converting and upgrading an existing DC is that if anything goes wrong, you might end up loosing your entire domain. It's much safer to install a clean VM, join it do the domain, make it a second DC, let it synchronize, and move the FSMO roles.

After that, you can decide whether to retire the old server or upgrade it to be a backup DC. It's recommended to have at least two domain controllers, and having them on separate hardware minimazes the risk of both going down at the same time.

  • Thank you! We actually did buy a new server to move the DC to and virtualize, as we needed another server for another project, so I tried to kill 2 birds with one stone and buy a nice beefy host to support both the new server and migrating the DC. In addition, I can promote the new DC to be the main DC and have the old one retire or be a backup? If so, all devices running DHCP would update to receive the new primary DC, but anything set static would need a manual update to get the new DNS servers, right? – TylerMillerRBC Aug 20 '19 at 16:51

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