Hi @Ahmed Salem
Thank you for posting your question in Microsoft Q&A.
We understand that you are considering about Exchange Server SE licensing. I will address each question individually to ensure clarity and thoroughness:
Is it required to purchase a new server license with SA before or after the upgrade?
Yes, you are required to purchase a new Exchange Server Subscription Edition license, and it must be purchased before you perform the upgrade on your production server. The old model of a one-time perpetual license with optional Software Assurance (SA) is gone. The Subscription Edition (SE) requires a subscription license, which is a recurring cost. This subscription includes the rights to support, updates, and future versions, effectively replacing the need for separate SA.
For compliance: To be legally compliant, you must have a valid license for the software you are running. Upgrading your server to Exchange SE without having the corresponding subscription license would put you out of compliance.
Can we just run the server while the mailboxes are assigned the Office 365 licenses? Unfortunately, the Office 365 licenses cover the users, not the server. You cannot legally run a production Exchange SE server that hosts mailboxes without its own subscription license.
Do I need to purchase server CALs alongside the Office 365 licenses assigned to the user?
You do not need to purchase separate Exchange Server Client Access Licenses (CALs) for users who are assigned a Microsoft 365 E3 license.
The reason is that your Microsoft 365 E3 licenses include "CAL equivalency rights.". This means that for licensing purposes, a user with an active M365 E3 license is already considered to have a valid CAL to access your on-premises Exchange Server. This is a key benefit for organizations running a hybrid environment, as it prevents you from having to license the same user twice (once for the cloud and again for on-premises).
Server License: You must buy a subscription for the server software itself.
User CALs: You are covered by the users' existing M365 E3 licenses
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