📚 How to Plan Your Upgrade to Exchange Server Subscription Edition
Welcome back, Exchange admins and hybrid champions!
Now that we know Exchange Server Subscription Edition (SE) is the new path forward for on-prem mail, it's time to get practical: How do you get there?
Here's your quick-start roadmap to plan a smooth upgrade from Exchange 2016 or 2019 to SE.
🗂️ 1. Understand Your Starting Point
First things first:
✅ Which version are you running today?
✅ Are you hybrid or fully on-prem?
✅ Are your servers fully patched?
✅ Which version are you running today?
✅ Are you hybrid or fully on-prem?
✅ Are your servers fully patched?
Remember: Microsoft wants you to be on Exchange Server 2019 CU14 or later to be eligible for an in-place upgrade to SE. Older versions will need a side-by-side migration.
🔑 2. Get Your Licensing in Order
With SE, perpetual licenses are gone — you'll need a valid subscription license.
Start the conversation with your licensing partner now. You don't want surprises when your current agreement expires.
Start the conversation with your licensing partner now. You don't want surprises when your current agreement expires.
🏗️ 3. Plan for the In-Place Upgrade
One of the biggest perks of SE:
✅ In-place upgrades from Exchange 2019!
✅ In-place upgrades from Exchange 2019!
No more swing servers or moving mailboxes. But there's a catch:
- You must run on supported OS versions — Windows Server 2022 is recommended.
- Your hardware must meet the requirements.
📌 Tip: Always back up before the upgrade. Practice in a lab if you can.
🔒 4. Modernize Security
Exchange SE will enforce a more secure baseline:
✅ Use TLS 1.2 or higher
✅ Ensure you've disabled legacy protocols (POP, IMAP if unused)
✅ Review your certificate strategy — are you ready for MTA-STS, DANE, or other newer security models?
✅ Use TLS 1.2 or higher
✅ Ensure you've disabled legacy protocols (POP, IMAP if unused)
✅ Review your certificate strategy — are you ready for MTA-STS, DANE, or other newer security models?
🔄 5. Prepare Your Hybrid Environment
If you're hybrid with Exchange Online:
✅ Update your Hybrid Agent
✅ Check OAuth configurations
✅ Verify Autodiscover and mail flow — small missteps here can cause big headaches.
✅ Update your Hybrid Agent
✅ Check OAuth configurations
✅ Verify Autodiscover and mail flow — small missteps here can cause big headaches.
📅 6. Communicate & Schedule
✔️ Schedule maintenance windows
✔️ Inform stakeholders — SE upgrades require downtime
✔️ Test, test, test — don't skip test mail flow and client connectivity.
✔️ Inform stakeholders — SE upgrades require downtime
✔️ Test, test, test — don't skip test mail flow and client connectivity.
🗒️ My Take
The Exchange SE upgrade is a welcome evolution: less migration pain, more security, and a clearer path forward for those who can't go fully cloud yet.
But remember: staying on SE means you must stay up-to-date — no more "set and forget." If you've been lax with updates in the past, now's the time to build that patching culture.
✨ What's Next on Lab365
✅ How to test your in-place upgrade before going live
✅ Licensing gotchas for Exchange SE — and how to avoid them
✅ Best practices for Exchange SE in a hybrid setup
✅ Securing your SE servers: A checklist
✅ Licensing gotchas for Exchange SE — and how to avoid them
✅ Best practices for Exchange SE in a hybrid setup
✅ Securing your SE servers: A checklist
💬 Have you started planning your move to Exchange SE? Drop your experiences in the comments — or let's discuss your challenges together!
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