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Navigating the End of Exchange 2019: Your Path to Exchange Server Subscription Edition or Microsoft 365

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Microsoft Exchange Server 2019’s end of life is approaching, marking a significant transition point for organizations worldwide. As IT administrators and decision-makers prepare for this change, understanding your migration options and preparation requirements becomes critical for maintaining seamless email operations. 

If you are still using Exchange 2019 – reach out to us to talk about your options for either continued operations using Exchange SE, or migration to M365.

Understanding Exchange 2019’s End of Life

Microsoft Exchange Server 2019 will reach its end of mainstream support, meaning organizations will no longer receive security updates, bug fixes, or technical support.

Exchange Server Subscription Edition: A New Licensing Model

Microsoft Exchange Server Subscription Edition (SE) represents a fundamental shift in how Exchange Server is licensed and deployed. Unlike traditional perpetual licensing, Exchange SE operates on a subscription-based model that provides continuous updates and support while maintaining on-premises control of your email infrastructure.

Environment Requirements for Exchange SE

Before migrating to Exchange Server Subscription Edition, your environment must meet specific technical prerequisites:

Active Directory Requirements:

  • Compatible Active Directory Domain Services version
  • Proper schema extensions and forest preparation
  • Adequate domain and forest functional levels

Windows Server Compatibility:

  • Supported Windows Server versions for hosting Exchange SE
  • Current security updates and patches
  • Sufficient hardware resources to support the new version

Network Infrastructure:

  • Proper network connectivity and bandwidth
  • Required ports and protocols configured
  • Certificate management for secure communications

Preparing Your Environment: A Step-by-Step Approach

1. Upgrade to the Latest Cumulative Update

If you’re currently running Exchange 2019, upgrading to Cumulative Update 15 (CU15) is absolutely essential. This update serves as a prerequisite for Exchange SE migration and ensures your current environment has the latest security patches and compatibility improvements.

2. Verify System Compatibility

Conduct a thorough compatibility assessment of your current infrastructure. This includes validating that your Active Directory and Windows Server versions align with Exchange SE requirements. Any incompatible components must be upgraded before proceeding with the migration.

3. Prepare Active Directory Infrastructure

Active Directory preparation involves several critical steps:

To ease the in-place upgrade process from Exchange 2019 to Exchange SE RTM, the following is true when comparing Exchange SE RTM to Exchange 2019 CU15:

  • No features were removed or added.
  • No Active Directory schema changes (/PrepareAD might be required if upgrading from CU14).
  • No installation prerequisites were changed.
  • No new license keys are required.

The following are the differences from Exchange 2019 CU15:

  • The License agreement (an RTF file shown only in the GUI version of Setup) was updated.
  • The name was changed from Microsoft Exchange Server 2019 to Microsoft Exchange Server Subscription Edition.
  • The build and version numbers were updated.
  • Updates released since Exchange 2019 CU15 are integrated into Exchange SE RTM (this happens in every CU update).
  • Configuring necessary containers and organizational units
  • Ensuring proper permissions and security groups are in place
  • Validating domain controller health and replication

4. Strategic Decision Making

Organizations face a crucial choice between Exchange Server Subscription Edition and migrating to Exchange Online as part of Microsoft 365. This decision should consider several factors:

Business Requirements:

  • Data sovereignty and compliance needs
  • Integration with existing on-premises systems
  • Customization and control requirements

Resource Considerations:

  • Available IT staff and expertise
  • Infrastructure maintenance capabilities
  • Budget allocation for licensing and support

Timeline Constraints:

  • Migration complexity and duration
  • Business continuity requirements
  • Training and adoption timelines

5. Understanding the New Licensing Structure

Exchange SE introduces a subscription-based licensing model that differs significantly from traditional perpetual licenses. Organizations need licenses with active Software Assurance or must transition to subscription-based licensing. This change affects budgeting, procurement processes, and long-term cost planning.

6. Third-Party Tool Assessment

Email infrastructure often relies on various third-party solutions for signatures, compliance, backup, and security. Evaluate the compatibility of these tools with both Exchange SE and Exchange Online:

  • Email signature management solutions
  • Compliance and archiving tools
  • Backup and disaster recovery systems
  • Security and anti-spam solutions
  • Mobile device management platforms

7. Testing and Validation

Before full deployment, establish a testing environment to validate critical functionalities:

Mail Flow Testing:

  • Internal and external email delivery
  • Routing and transport rules
  • Anti-spam and anti-malware functionality

Integration Validation:

  • Application connectivity
  • Authentication mechanisms
  • Directory synchronization (if applicable)

Performance Assessment:

  • System responsiveness under load
  • Database performance and storage requirements
  • Network bandwidth utilization

The Microsoft 365 Alternative

While Exchange SE maintains on-premises email infrastructure, Microsoft 365 offers a cloud-based alternative that eliminates many maintenance responsibilities. Exchange Online provides:

Advantages:

  • Reduced infrastructure management overhead
  • Automatic updates and security patches
  • Scalability and global accessibility
  • Integration with Microsoft 365 productivity suite

Considerations:

  • Internet connectivity requirements
  • Data location and compliance implications
  • Migration complexity from on-premises systems
  • Ongoing subscription costs

Making the Right Choice for Your Organization

The decision between Exchange SE and Microsoft 365 depends on your organization’s specific needs, resources, and strategic direction. Consider these factors:

Choose Exchange SE if:

  • You require on-premises data control
  • Existing infrastructure investments are significant
  • Compliance mandates local data storage
  • You have dedicated IT resources for maintenance

Choose Microsoft 365 if:

  • You want to reduce infrastructure management
  • Remote work and collaboration are priorities
  • Scalability and automatic updates are valuable
  • You’re looking to modernize productivity tools

Conclusion

The end of Microsoft Exchange 2019 support creates both challenges and opportunities for organizations. Whether you choose Exchange Server Subscription Edition or migrate to Microsoft 365, proper preparation and planning are essential for success.

Take action now to assess your environment, understand your options, and develop a comprehensive migration strategy. The transition period provides an excellent opportunity to modernize your email infrastructure and improve organizational productivity.

Remember that each organization’s needs are unique, and the best path forward depends on your specific requirements, resources, and strategic objectives. Consider engaging with Microsoft partners or consultants to ensure your migration is executed smoothly and efficiently.