Joining Server 2008 Standard with AD LDS to Server 2019 AD DS with Domain Function Level 2008

Question

So I have set up a New DC Server 2019 Datacenter with AD DS role installed and configured, accounts have been created for all users in the office, and a few are left to loin the Domain.

One of my concerns is that the one Server 2008 Standard is in a workgroup, running AD LDS. When I first joined this to the domain the DC was at Domain Function Level 2016, which caused a huge problem the Server was not operational after joining the 2008 Server to the domain. Had no backup and research did not help fix this issue. Rebuilt the server then rejoined the clients to the domain again, now coming to a few computers left is the one that started the problem, I think it was the Domain Function Level on the DC was set to 2016, when I have a 2008 Server in a workgroup and part of the error message was about server 2003 with service pack 3 installed. Lesson learned, now have a backup of the DC a Full backup for full bare metal restore if needed.

What if any issue would now come from joining this server to the domain? Can you join a 2008 Standard Server running AD LDS in a workgroup to a Domain DC, Server 2019 AD DS with Domain Function Level at 2008?

On a Server that has AD LDS running can you install AD DS and migrate AD LDS to AD? Then promote that to a BDC? Any suggestion would be helpful.

Just to be clear, The Server 2008 Standard running AD LDS is in a workgroup, The DC is Server 2019 with AD DS is the domain. Need to join the 2008 Server to the domain without breaking AD like I did last time. I was able to recover had to rebuild the rejoin to the network. I have it doing a full backup every day just in case I need it to restore. I did not set all of this up with I am in charge of setting up the domain and securing the network. This is one problem child I have to deal with.

Answer 1

Shouldn't be a problem but you might want to try in a test environment. Also confirm the health on 2008 is good (2008 vista kernel was notorious for servicing corruption)

verify system and servicing health by running;
sfc /scannow

also system update readiness tool

https://www.microsoft.com/en-us/download/details.aspx?id=22931

Then check for errors in;
%SYSTEMROOT%\Logs\CBS\CheckSUR.log

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Answer 2

A 2008 member server would not be a problem in a 2016 DFL domain. 2016 domain functional level is the highest level even with Server 2019. As to compatibility for a 2019 domain controller.

The two prerequisites to introducing the first 2019 domain controller are that domain functional level needs to be 2008 or higher and older sysvol FRS replication needs to have been migrated to DFSR
https://techcommunity.microsoft.com/t5/Storage-at-Microsoft/Streamlined-Migration-of-FRS-to-DFSR-SYSVOL/ba-p/425405

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Answer 3

Hi,

Just checking in to see if the information provided was helpful.

Please let us know if you would like further assistance.

Best Regards,
Vicky

Answer 4

Just to be clear, The Server 2008 Standard running AD LDS is in a workgroup, The DC is Server 2019 with AD DS is the domain. Need to join the 2008 Server to the domain without breaking AD, the current Domain Function Level is set to 2008 on the DC. Will this cause any problems? Thank you for your help.

Answer 5

You may have better luck standing up a new one, patch fully, join existing domain, then restore a backup.
https://learn.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2008-R2-and-2008/cc733082(v=ws.11)?redirectedfrom=MSDN

then sync (if required)
https://learn.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2008-R2-and-2008/cc770408(v=ws.10)

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