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Step-by-Step Guide: Active Directory Migration from Windows Server 2008 to Windows Server 2019

As you may already know, Windows Server 2008 and 2008 R2 products reached End of Extended support on 1/14/2020. So if your Active Directory is running on Windows Server 2008, It is time to look for upgrade options.

In this blog post, I am going to demonstrate how to migrate Active Directory from Windows Server 2008 to Windows Server 2019.

AD Migration task itself is very straight forward. But there are other things you need to consider before you do an AD migration. Below I listed a checklist you can use on many occasions.

Active Directory Migration Check List

• Evaluate business requirement for Active Directory migration
• Perform Audit on Existing Active Directory Infrastructure to make sure there are no existing health issues
• Provide Plan for implementation Process
• Prepare Physical / Virtual resources for Domain Controller
• Install Windows server 2019 Standard / Datacenter
• Patch Servers with latest Windows Updates
• Assign Dedicate IP address to Domain Controller
• Install AD DS Role
• Migrate Application and Server Roles from the Existing Domain Controllers.
• Migrate FSMO roles to new Domain Controllers
• Add New Domain controllers to the Existing Monitoring system
• Add New Domain controllers to the Existing DR Solution
• Decommission old domain controllers
• Raise the Domain and Forest Functional level
• On-Going Maintenance (Group Policy Review, New Features Implementations, Identify and fix active directory infrastructure issues)

If organizations running AD DS, it’s obvious it to have active directory integrated applications. Some of those may use it just for LDAP authentication and some may use advanced integration with modified active directory schema. with active directory migration, some of these applications may require modifications or upgrades to match with the new AD DS version. Therefor before the implementation process, it is important to recognize these active directory integrated applications and evaluate its impact on the migration.

LDAP Connection String Modifications – To use single-sign-on (SSO) with applications it may use LDAP connections to domain controllers. sometimes applications use hardcoded hostnames or IP addresses of domain controllers to define the connections. If domain migration involves IP address changes and Hostname changes, alternation to these records will be needed.

Schema Version Changes – Some legacy applications only support certain versions of active directory schema. This is specifically applying for custom made active directory integrated applications. This is very rare but I have to face these in my active directory migrations projects. Therefore if it’s not well-known applications, check with the application vendor if it supported new AD DS schema version.

Application Migrations – Some organizations have legacy application versions that no longer support or develop by its vendor. There are occasions where these types of issues turn to be bottlenecks for AD Migration projects. Once I was working on AD DS 2003 to AD DS 2012 R2 migration project. The organization had a legacy application that runs on windows server 2000 system. AD DS 2012 R2 does not support windows server 2000-member servers. The vendor who created the application no longer in business. Then we had to users to similar type application which supports new operating systems before we start the Active Directory migrations.

Server Roles/Applications installed on Domain Controllers – In the majority of the cases, once FSMO roles migrated to new domain controllers, old domain controllers will be decommissioned. Even though Microsoft recommends not to install applications or other server roles in domain controllers, people still do it. Some of the common roles installed in domain controllers are DHCP, File Servers, Licensing Server. If existing domain controllers are subject decommission these applications and server roles need to migrate new servers.

Most Common Questions About AD Migrations

In below I listed some of the most common questions I get about AD migration,

1. Can I keep the same IP address for the PDC? Yes, you can. Active Directory fully supports for IP address changes. Once FDMO role migration is completed, you can swap the IP addresses of Domain Controllers.
2. Can I downgrade forest/domain functional levels? Yes, you can do it from Windows server 2008 R2.
3. Do I need to migrate the DNS role? No, it is part of the AD. When you add a new domain controller, you can make it as DNS server too.
4. Do I need to change SYSVOL replication from FRS to DFS? If your domain is built based on Windows server 2008 or Windows Server 2008 R2, you are already using DFS for SYSVOL replication. If you originally migrated from Windows server 2003, it’s more likely you are still using FRS. In that case, after the migration, you can also change the SYSVOL replication method from FRS to DFS. I already have a blog post covering this topic https://www.rebeladmin.com/2015/04/step-by-step-guide-for-upgrading-sysvol-replication-to-dfsr-distributed-file-system-replication/
5. Can I keep Windows 2008 Domain Controllers and upgrade forest and domain functional level to Windows Server 2016? (Windows server 2019 does not have the forest and domain functional level name as Windows server 2019. it is still called Windows server 2016) – No, you can’t. Before forest and domain functional level upgrade, you need to decommission Windows server 2008 domain controllers.

Demo Environment

Active Directory demo topology

As per the above figure, rebeladmin.com domain has two domain controllers. The FSMO role holder (REBEL-DC2008) is running a domain controller based on windows server 2008. Domain and forest functional level currently operating at Windows server 2008. A new domain controller with Windows Server 2019 (REBEL-DC2019) will be introduced and it will be the new FSMO role holder for the domain. once FSMO role migration completed, Domain controller running windows server 2008 will be decommissioned. After that forest and domain, the functional level will be raised to the windows server 2019.

Note – When you introduce new domain controllers to the existing infrastructure it is recommended to introduce to the forest root level first and then go to the domain tree levels.

[Read more…] about Step-by-Step Guide: Active Directory Migration from Windows Server 2008 to Windows Server 2019

Mastering Active Directory, Second Edition Released!

As most of you were aware, I published my book "Mastering Active Directory" back in, 2017. When I released it, I had my doubts! It was my first book even though I was writing to blogs for many years. But over the last 2 years, I had many positive feedbacks. Thousands of people all around the global read this book. Lots of them requested another book. So Yes! I heard it loud and clear. 

I glad to announce the public release of my second book, "Mastering Active Directory, Second Edition" today. It is available for purchase worldwide now.

I also take this opportunity to thanks all my readers who believed in me. It is you who encouraged me to release another edition this soon. 

What Is new in the second edition? 

The new content for this edition is covering,

• Tips to Design your Hybrid AD environment by evaluating business and technology requirements 

• Deep dive into different authentication methods which can use in Hybrid AD environment

• How to protect sensitive data in a hybrid environment using Azure Information Protection

• Learn about protecting identities in Hybrid AD environment 

• Integrate with Azure Active Directory and Manage identities in Hybrid Environment using Azure Active Directory PowerShell for Graph module

Book Name: Mastering Active Directory, Second Edition

ISBN: 978-1789800203

Number of Pages: 786

Publisher: Packt Publishing

Book is available in paperback and kindle format.

It also can access via subscriptions, 

https://www.packtpub.com/cloud-networking/mastering-active-directory-second-edition

Step-by-Step Guide to Active Directory “Protected Users security group”

The Protected Users security group was introduced with Windows Server 2012 R2 and continued in Windows Server 2019. This group was developed to provide better protection for high privileged accounts from credential theft attacks. Members of this group have non-configurable protection applied. In order to use the Protected Users group, PDC should be running with a minimum of Windows Server 2012 R2 and the client computers should be running with a minimum of Windows 8.1 or Windows 2012 R2.

If a member of this group logs into Windows 8.1, Windows Server 2012 R2, Windows 10, Windows Server 2016 or Windows server 2019, we can expect the following:

• Members of this group cannot use NTLM, digest authentication, or CredSSP for authentication. Plain text passwords are not cached. So, any of the devices using these protocols will fail to authenticate to the domain.

• Kerberos long-term keys not cached. For accounts in this group, the Kerberos protocol verifies authentication at each request (the TGT acquired at log on).

• Sign-in is offline. A cached verifier is not created at sign-in.

For the Protected Users group feature, it is not a must to have a domain or forest functional level run on Windows Server 2012 R2 or higher (Windows Server 2008 is the minimum as Kerberos needs to use AES). The only requirement is to run the PDC emulator FSMO role in the Windows Server 2012 R2 domain controller.

If the AD environment uses Windows Server 2012 R2 or Windows Server 2016 domain functional levels, it provides additional protections with Protected User groups, as:

• No NTLM authentication

• No DES or RC4 encryption in Kerberos pre-authentication

• No delegation using the unconstrained or constrained method

• No Kerberos TGT valid more than 4 hours

[su_note]Service accounts and computers cannot be members of the Protected Users' security group. These accounts can be protected using different features, such as policy silos, which I will explain later in this chapter.[/su_note]

To start with, we can review the Protected Users security group using the following command:

Get-ADGroup -Identity "Protected Users"

The following screenshot shows the output for the preceding command:

We can add users to the Protected Users group using ADAC, ADUC MMC, and PowerShell. This group is located in the default Users container in AD.

In here, we are going to add the user account Adam in to the Protected Users group using the following command:

Get-ADGroup -Identity "Protected Users" | Add-ADGroupMember –Members "CN=Adam,CN=Users,DC=rebeladmin,DC=com"

The first part of the command will retrieve the group and the second part will add the user Adam to it. [Read more…] about Step-by-Step Guide to Active Directory “Protected Users security group”

Step-by-Step Guide to Migrate from Active Directory 2012 R2 to Active Directory 2019 (PowerShell Guide)

Windows server 2019 was available for public (GA) from early oct 2018. In past i have written many articles about domain migrations by covering different Active Directory versions. So, it is time me to write about AD 2019 migrations. In this demo I am going to demonstrate how to migrate from Active Directory 2012 R2 to Active Directory 2019. The same procedure is going to apply for any AD version from Windows Server 2008.   

Migration itself is very straight forward task. But there are other things you need to consider before you do an AD migration. In below I listed a checklist you can use in many occasions.

• Evaluate business requirement for active directory migration 

• Perform Audit on Existing Active Directory Infrastructure

• Provide Plan for implementation Process

• Prepare Physical / Virtual resources for Domain Controller

• Install Windows server 2019 Standard / Datacenter

• Patch Servers with latest Windows Updates

• Assign Dedicate IP address to Domain Controller

• Install AD DS Role

• Migrate Application and Server Roles from the Existing Domain Controllers.

• Migrate FSMO roles to new Domain Controllers

• Add New Domain controllers to the Existing Monitoring system

• Add New Domain controllers to the Existing DR Solution

• Decommission old domain controllers 

• Raise the Domain and Forest Functional level

• On Going Maintenance 

As per the above figure therebeladmin.com domain has two domain controllers.  In here, the FSMO role holder is running windows server 2012 R2. Domain and forest functional level currently operating at Windows server 2012 R2. A new domain controller with Windows server 2019 will be introduce and it will be the new FSMO role holder for the domain. once FSMO role migration completed, Domain controller running windows server 2012 R2 will be decommissioned. After that forest and domain function level will raised to the windows server 2019. 
In the demonstration, REBEL-DC2012 is the domain controller with windows server 2012 R2 and REBEL-DC2016 is the domain controller with windows server 2019. 
 
[su_note]When you introduce new domain controllers to the existing infrastructure it is recommended to introduce to the forest root level first and then go to the domain tree levels.[/su_note]
 
 
1. Log in to the Server 2019 as a member of local administrators group. 
2. Add server to the existing domain as member
 
 
3. After restart, log in to the server as Enterprise Administrator
4. Assign static IP address to the server
5. Launch the PowerShell Console as an Administrator
6. Before the configuration process, we need to install the AD DS Role in the given server. In order to do that we can use Following command. 
 
Install-WindowsFeature –Name AD-Domain-Services -IncludeManagementTools
 
 
7. Configure the new server as additional domain controller.
 
Install-ADDSDomainController
-CreateDnsDelegation:$false
-NoGlobalCatalog:$true
-InstallDns:$true
-DomainName "therebeladmin.com"
-SiteName "Default-First-Site-Name"
-ReplicationSourceDC "REBEL-DC2012.therebeladmin.com"
-DatabasePath "C:\Windows\NTDS"
-LogPath "C:\Windows\NTDS"
-NoRebootOnCompletion:$true
-SysvolPath "C:\Windows\SYSVOL"
-Force:$true
 
 
There are no line breaks for the command and I have listed it as above to allow readers to identify on the parameters clearly.
 

Argument

Description

Install-ADDSDomainController

This cmdlet will install the domain controller in active directory infrastructure.

-NoGlobalCatalog

If you do not need to create the domain controller as global catalog server, this parameter can use. By default, system will enable global catalog feature.

-SiteName

This Parameter can use to define the active directory site name.  the default value is Default-First-Site-Name

-DomainName

This parameter defines the FQDN for the active directory domain.

-ReplicationSourceDC

Using this parameter can define the active directory replication source. By default, it will use any available domain controller. But if need we can be specific.

Once execute the command it will ask for SafeModeAdministrator Password. Please use complex password to proceed. This will be used for DSRM.

8. After configuration completed, restart the system and log back in as administrator to check the AD DS status. 

Get-Service adws,kdc,netlogon,dns

Will confirm the status of the AD DS service. 

Get-ADDomainController -Filter * |  Format-Table Name, IPv4Address, Site

Will list down the domain controllers along with the IP address and Sites it belongs to.

9. Migrate all five FSMO roles to the New domain controller using following command,

Move-ADDirectoryServerOperationMasterRole -Identity REBEL-DC2019 -OperationMasterRole SchemaMaster, DomainNamingMaster, PDCEmulator, RIDMaster, InfrastructureMaster

In above the REBEL-DC2019 is domain controller running with windows server 2019. 

Once its completed, we can verify the new FSMO role holder using 

Netdom query fsmo

10. The new step of the process is to decommission the old windows domain controller which running with windows server 2012 R2. To do that execute the following command as enterprise administrator from the relevant DC. 

Uninstall-ADDSDomainController -DemoteOperationMasterRole -RemoveApplicationPartition

After execute the command it will ask to define password for the local administrator account.

Once its completed it will be a member server of the therebeladmin.com domain.

11. Next step is to raise the domain and forest functional level to windows server 2019. To do that can use the following commands.

To upgrade domain functional levels

Set-ADDomainMode –identity therebeladmin.com -DomainMode Windows2016Domain

To upgrade forest function levels

Set-ADForestMode -Identity therebeladmin.com -ForestMode Windows2016Forest

[su_note]With windows server 2019, there is no domain or forest functional level called windows2019. It is still 2016. [/su_note]

Now we have completed the migration from AD DS 2012R2 to AD DS 2019. Same steps apply when migrate from windows server 2008, Windows server 2008 R2, Windows server 2012 & Windows server 2016.

12. After the migration completes, we still need to verify if its completes successfully. 

Get-ADDomain | fl Name,DomainMode

This command will show the current Domain functional level of the domain after the migration. 

Get-ADForest | fl Name,ForestMode

Above command will show the current forest functional level of the domain. 

This marks the end of this blog post. Hope this was useful. If you have any questions feel free to contact me on rebeladm@live.com also follow me on twitter @rebeladm to get updates about new blog posts.

Step-by-Step Guide to install Active Directory in Windows Server 2019 (PowerShell Guide)

Finally waiting game is over, Windows server 2019 is now available for public. So, it is time to start planning for your production migrations. In this demo I am going to demonstrate how we can setup Active Directory 2019 with new AD forest. I will discuss new features of AD 2019 in a later post. 

In below, I created a checklist which we can use to track the progress of installation. 

Active Directory Domain Service Installation Check List for First Domain Controller

Produce Active Directory Design Document 

Prepare Physical / Virtual resources for Domain Controller

Install Windows server 2019 Standard / Datacenter

Patch Servers with latest Windows Updates

Assign Dedicate IP address to Domain Controller

Install AD DS Role

Configure AD DS according to Design

Review logs to verify the healthy AD DS installation and configuration

Configure Service and Performance Monitoring 

AD DS Backup / DR Configuration 

Produce System Documentation 

Design Topology
 
As explain in the above figure, in my demo environment, rebeladmin.com will be the forest root domain. The first domain controller install on the forest will hold all five FSMO roles. Once additional domain controllers are in place you can place them in appropriate locations. 
 
1. To start the configuration, I logged in to Windows server 2019 server as local administrator.