Upgrade from Exchange 2013+O365 hybrid to Exchange 2019+O365 hybrid

Aritra Das 21 Reputation points


My environment currently has Exchange 2013 in coexistence with O365 (Hybrid). 2 mailbox servers + 2 CAS servers. MX record pointed to third party Mail gateway which routes to On prem servers.
Looking to upgrade to Exchange 2019 to be in coexistence with O365.
Can somebody help with the planning and steps to be followed for a smooth Migration. There are indeed a lot of articles on the internet, but cant understand where to start with or how to create a plan to start the transition.
Thank you in advance.

Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
7,227 questions
Microsoft Exchange Hybrid Management
Microsoft Exchange Hybrid Management
Microsoft Exchange: Microsoft messaging and collaboration software.Hybrid Management: Organizing, handling, directing or controlling hybrid deployments.
1,802 questions
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Accepted answer
  1. KyleXu-MSFT 26,201 Reputation points

    @Aritra Das

    You could take steps below to update;

    Update Exchange 2013 to CU 21 or later for coexist with Exchange 2019: Supported coexistence scenarios for Exchange 2019

    Install Exchange 2019 coexist with Exchange 2013, then migrate all Exchange on-premises mailboxes(Include arbitration mailboxes) to Exchange 2019.

    Configure Exchange 2019 as Internet facing server and rerun HCW to choose Exchange 2019 as hybrid server.

    Shutdown Exchange 2013, check whether there exist issue. If there doesn't exist an issue, you could uninstall those Exchange 2013 server.

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