Server Migration software to migrate roles

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Hello Experts,

We are migrating a lot of windows 2008 R2 stand alone servers, some with hyper-v.  The VM's are running the same OS.  Is there any third party software that can move all of the roles, features and any software currently installed to a newer server such as Windows Server 2016 or 2019?  I haven't really heard of something like this but figured this would be the best place to ask first.

thank you,

-GTS
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Adam BrownSenior Systems Admin
Top Expert 2010

Commented:
There are no specific tools that will do everything, but the vast majority of migrations are pretty simple to accomplish without tools. The major exception here is a migration that moves the environment to a new AD forest. This is very complicated and the Quest Migration Tools or ADMT will help with that. The process for migrating from one server version to another depends on the role. For instance:
1. AD Migration - Just add a new DC, make sure replication is working, then migrate FSMO roles,
2. DNS - If you have AD Integrated zones, see step 1...Otherwise, configure a new DNS server, grant transfer permissions to it, them replicate the zone.
3. RDS - More complicated, but essentially just install the apps you need on the new server after performing the RD Services Install Wizard in Server Manager
4. DHCP - Back up the DHCP data on one server, restore to new server (shut down DHCP on old server immediately

And so one. What roles do you need to migrate over?
Bradley FoxLAN/WAN Systems Administrator

Commented:
Depending on the role you are moving there are different utilities available.  Unfortunately, there is no one tool does it all for this type of migration.  Most roles can be transferred to another server pretty easily.  Here are some walk-throughs for the most common roles.

File Server - https://docs.microsoft.com/en-us/windows-server/storage/storage-migration-service/migrate-data
NPS/Radius - https://docs.microsoft.com/en-us/windows-server/networking/technologies/nps/nps-manage-export
IIS - https://www.iis.net/downloads/community/2013/04/iis-easy-migration-tool-iemt
DHCP - https://www.faqforge.com/windows-server-2016/migrate-dhcp-windows-server-2012-r2-server-2016/
AD - Promote the new server then demote the old one.  If you have FSMO roles on the old server transfer those before demotion https://theitbros.com/transfer-fsmo-roles-using-powershell/

Author

Commented:
You pretty much got all of them.  The one big issue we have is the software being used on some of these servers is no longer current and the software company's that supported it are no longer around.  We need to have the software migrated as well but with out a install package or instructions on how to install and configure we are faced with a problem.
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Scott SilvaNetwork Administrator

Commented:
Old software is always a pain in migrations... Did the installers not get kept? If you do have install disks, I would spin up a test system and see if the software still works with the new os... If it doesn't, or you can't reinstall, you are going to either have to find something else, or live with old servers off of support and just do your best with firewalls and restrictions to minimize or mitigate any possible future issues that might come up... I know a few companies still running XP boxes because the hardware they control is long out of support and VERY expensive to replace...

Commented:
You could likely convert the physical server to virtual servers if you were using VM Ware.  https://www.vmware.com/support/converter/doc/conv_sa_60_rel_notes.html
Bradley FoxLAN/WAN Systems Administrator

Commented:
I wouldn't convert them to VMs, I assume the purpose is to get rid of the 2008 R2 servers because M$ is stopping support on 1/1/2020.

I've used this on Windows 10 in the past with moderate success.  I'm not sure if/how it would work on a server OS but it's worth a shot if you have no other way to move installed software.

https://pcmover-10.laplink.com/
kevinhsiehNetwork Engineer

Commented:
For servers with software that is no longer supported, I would first convert the server to a VM. Take a snapshot of the VM, and then try an in -place OS upgrade. If it works, that's great and delete the snapshot. If it doesn't work, revert the snapshot and no harm no foul.
Network Administrator
Commented:
Just remember, to go from 2008 R2 to 2016 takes 2 in place upgrades... First you have to go to 2012 R2, then 2016

Author

Commented:
a lot of great information.  Scott Silva, have you ever tried the in place migration as described above?
Scott SilvaNetwork Administrator

Commented:
I have on a few very non critical servers, but it isn't recommended by Microsoft.

If you do think you want to try, make sure you have a good bare metal backup to test on, or a clones system if it is virtual to make sure it works first.

Author

Commented:
they are all VM's i want to upgrade. The VM host i will just reload.

Commented:
Typically the legacy software will break upgrading from server 2098 to 2012 and 2016.  Yws server 2008 is end of life.  We support many legacy programs and you might need to fence the 2008 servers off until you come up with a solution.  Virtualizing the physical 2008 servers is the best way to keep it going and get them onto reliable hardware.
Philip ElderTechnical Architect - HA/Compute/Storage

Commented:
Active Directory is pretty straight forward. Install the role, promote into the domain, transfer the FSMO roles, and verify replication. DNS would move along with AD.

DHCP is simple, just export the DHCP database and import it on the new 2016 or 2019 server.

No multi-steps required for those roles.

Storage servers can use the new Storage Migration Service (SMS). It works really well.

For physical to virtual (P2V) we use Veeam or StorageCraft ShadowProtect.

As far as VM from host to host that's a good question. Hyper-V Replica is one option depending on host version.

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