Upgrading Windows Exchange Server 2016 and 2019 – Choose Your Migration Path Before End of Life

On October 14, 2025, support for Windows Exchange Server 2016 and Exchange Server 2019 will officially end. While your current installations will continue to run, they will no longer receive critical updates—leaving your organization vulnerable to security risks and without access to technical support. To protect your systems, now is the time to plan your next step: migrate to Exchange Online or Microsoft 365, or upgrade to Exchange Server SE. No matter which option you choose, a Microsoft consultant can help guide you through a secure and seamless transition.

Microsoft Exchange Servers 2016, 2019 End of Life

If you don’t take action before the October 14 end-of-support date for Exchange Server 2016 and 2019, here’s what will happen:

  • No technical support from Microsoft
  • No bug fixes, which could affect server stability and performance
  • No security updates, leaving your system exposed to potential breaches
  • No time zone updates

Without these protections, your servers could become an easy target for cybercriminals and other threats. That’s why Microsoft strongly recommends planning your next steps now.

Migrating to Exchange Online or Microsoft 365

Microsoft recommends the simplest and most future-ready option: fully migrating to Exchange Online or Microsoft 365. Moving to the cloud unlocks powerful new features—including advanced generative AI tools like CoPilot—that aren’t available on-premises. Microsoft also provides step-by-step guidance for global administrators to manage the migration process go Microsoft 365 or Exchange Online. 

Update to Exchange Server SE

If you’re still running Exchange 2016, you’ll first need to migrate to Exchange 2019. From there, you can complete an in-place upgrade to Exchange Server SE once it’s available.

  • A direct upgrade from Exchange 2016 CU23 to Exchange SE RTM is technically possible, but the timeline between SE’s release and the Exchange 2016 CU23 end-of-support date is too short to be practical.
  • An in-place upgrade from Exchange 2016 CU23 to SE is not supported.
  • Once you’ve upgraded to Exchange 2019 CU15, you can safely decommission your Exchange 2016 servers.

Working with a Microsoft Consultant

A Microsoft consultant can help you evaluate the right path for your organization and ensure a smooth transition with minimal disruption. With Windows 10 also reaching end of support on October 14, a consultant can assist in addressing both challenges together and help safeguard your critical operations.

Anders Technology advisors work with clients on server migrations and monitoring to keep your users protected and productive. Learn more about how our advisors can help, and the associated costs, by requesting a meeting below.

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