Troubleshooting Microsoft Exchange Server 2019 Installation on Windows Server 2022

Windows Server administrators, hold onto your keyboards. If you've been tasked with installing Microsoft Exchange Server 2019 on a Windows Server 2022 environment and find yourself stuck in a mire of error logs, this article has you covered. We're diving into a real-world installation scenario that played out on the Spiceworks forums, identifying key challenges and suggesting concrete solutions. Let’s unravel this tangle, bit by bit.

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The Core Problem​

A user attempted to install Exchange Server 2019 on a Windows Server 2022 machine. Despite following an extensive installation guide with meticulous preparation, the process failed during the Active Directory schema extension step. The central error was logged while executing the /PrepareAD command, which is a critical part of configuring Active Directory for Exchange Server.
This was exacerbated by several factors such as:

• Mismatched forest and domain functional levels.
• Incorrectly prepped Active Directory schema versions.
• Missing pre-requisites like Visual C++ Redistributables.
• Dependency issues with accounts and permissions in the Enterprise Admins group.

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Breaking Down the Key Errors​

1. Active Directory Functional Level​

Errors like this one appeared:

"The forest functional level of the current Active Directory forest is not Windows Server 2012 R2 or later."

Cause: Exchange 2019 requires a minimum forest and domain functional level of Windows Server 2012 R2. Without this, the setup cannot proceed to prepare Active Directory.
Solution:

• Check your functional levels with the PowerShell command:
  

  powershell
  
    Get-ADForest | Select-Object DomainMode, ForestMode

• If either is below 2012 R2, upgrade functional levels. Be cautious—this cannot be reversed. Run:
  

  powershell
  
    Set-ADForestMode –Identity <DomainName> –ForestMode Windows2012R2Forest
  
    Set-ADDomainMode –Identity <DomainName> –DomainMode Windows2012R2Domain

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2. Schema Version Mismatch​

Another error stated:

"The Active Directory organization configuration version (16762) is higher than Setup’s version (16760). Therefore, PrepareAD can’t be executed."

Cause: This mismatch occurs when a newer build of Exchange has already updated Active Directory, but the current installation is using an older build. For example, the reported setup was using Exchange 2019 CU12, while Active Directory had been prepped for a schema version associated with Exchange 2019 CU14.
Solution:

• Determine the schema version using:
  

  powershell
  
    Get-ADObject (Get-ADRootDSE).schemaNamingContext -Property rangeUpper

• Cross-reference the schema version with the Exchange CU matrix on official Microsoft documentation.
• Ensure you are running Setup.exe from the CU version that matches the schema preparation (in this case, CU14).

Pro Tip: Always download the latest cumulative update for Exchange before starting.

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3. Missing Critical Pre-requisites​

Errors flagged multiple missing dependencies:

• IIS URL Rewrite Extensions:

"IIS URL Rewrite Failed: Not Installed"

• Redistributables:

"Microsoft Visual C++ 2013 Failed: Visual C++ 2013 Redistributable"

Resolution:

• Download and install missing components from Microsoft.
  • IIS URL Rewrite: Found here.
  • Visual C++ Redistributables for 2012 and 2013: Found in the Microsoft Support Portal.
• Re-run any pre-requisite validation tools or scripts, such as SetupAssist.ps1 (referenced in the original post).

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4. Permissions Issue: Enterprise Admins Group​

Key error:

"Global updates need to be made to Active Directory, and the user account isn’t a member of the 'Enterprise Admins' group."

Cause: To prepare Active Directory, the executing user must belong to the Enterprise Admins group. Membership in Domain Admins or Schema Admins alone isn’t sufficient.
Solution:

• Check memberships:
  

  powershell
  
    Get-ADGroupMember "Enterprise Admins"

• Add the account to Enterprise Admins if missing:
  

  powershell
  
    Add-ADGroupMember -Identity "Enterprise Admins" -Members <AccountName>

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5. Critical Mailbox Errors​

Failures also included:

• "Valid Home MDB: Failed to find any critical mailboxes."
• "Valid Home Server Name: Failed to find any critical mailboxes."

These warnings typically arise in environments with incomplete or partially deployed Exchange configurations. They can also surface due to schema versions mismatched to current Active Directory data.
Solution:

• Ensure the /PrepareAD step completes successfully using the correct Exchange CU version.
• Verify the Exchange organization and database health using:
  

  powershell
  
    Get-MailboxDatabase

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Key Lessons From the Discussion Board​

• Use the Right CU Version: Always use the latest cumulative update for Exchange 2019 compatible with your environment. Setup.exe from outdated CUs may fail due to mismatched schema changes.
• Prepare in Sequence: Before running Exchange setup, ensure all pre-requisites (URLs, redistributables, functional levels) are fully met. Use validation scripts like SetupAssist.ps1 pre-emptively.
• Secure a Secondary Admin Account: Avoid relying on default administrator accounts. A dedicated Enterprise Admin account for installations can help isolate permission issues.

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Alternate Installation Tips​

If errors persist despite troubleshooting:

1. Run /PrepareAD directly on the domain controller for clearer logging.
2. Review Group Policy settings that could interfere with admin accounts.
3. Use event logs (Event Viewer > Application Logs) and Exchange setup logs for granular error analysis.

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Final Thoughts​

In the fight to install Exchange Server 2019, attention to detail is your first line of defense. By systematically ruling out issues with schema mismatches, missing components, and Active Directory functional levels, you can cut through the clutter and conquer errors like a pro.
Remember: patience, the right tools, and solid documentation from forums like Spiceworks (or here at WindowsForum.com!) can ease even the trickiest installs.
What other installation nightmares have you faced, and how did you triumph over them? Share your war stories in the comments!

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Source: Spiceworks Community Error installing exchange server 2019 on windows server 2022