Order for OS upgrade and SQL Server upgrade

Sameer Chhetri 0 Reputation points
2026-09-28T01:13:29.5866667+00:00

Hi Team,
Could you please let me know the correct or recommended order for upgrading Windows Server 2016 (to 2022) and SQL Server 2016 (to 2022), along with the risks (if any).

Thank you!

Windows for business | Windows Server | Devices and deployment | Set up, install, or upgrade
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  1. Daphne Huynh (WICLOUD CORPORATION) 1,550 Reputation points Microsoft External Staff Moderator
    2026-09-28T02:59:01.1433333+00:00

    Welcome to Microsoft Q&A!

    Thank you for providing the details of your upgrade scenario. I am happy to share the recommended approach based on Microsoft guidance.

    If Windows Server 2016 and SQL Server 2016 are installed on the same server, the recommended upgrade sequence is generally:

    1. Update SQL Server 2016 to SQL Server 2016 SP3 and the latest supported servicing level.
    2. Back up and validate the environment.
    3. Upgrade SQL Server 2016 SP3 to SQL Server 2022.
    4. Verify that SQL Server and all dependent applications are functioning correctly while the server is still running Windows Server 2016.
    5. Upgrade Windows Server 2016 to Windows Server 2022.
    6. Apply the latest Windows Server and SQL Server updates and perform a complete post-upgrade validation.

    The reason for upgrading SQL Server first is to maintain a supported configuration throughout the transition:

    • SQL Server 2022 is supported on Windows Server 2016.
    • SQL Server 2016 is not supported on Windows Server 2022.
    • A direct upgrade from SQL Server 2016 SP3 (or later) to SQL Server 2022 is supported.
    • Windows Server 2016 can be upgraded directly to Windows Server 2022 through a supported in-place upgrade path.

    Because of this, upgrading the operating system first would temporarily leave SQL Server 2016 running on Windows Server 2022, which is not a supported configuration.

    Before proceeding, I strongly recommend:

    • Verifying that your SQL Server edition and installed components support the upgrade path.
    • Reviewing any dependencies such as Always On Availability Groups, Failover Cluster Instances, replication, SSIS, SSAS, SSRS, or third-party applications.
    • Running a SQL Server upgrade assessment and checking for deprecated or discontinued features.
    • Taking and verifying full backups of all user and system databases, including master, model, and msdb.
    • Running DBCC CHECKDB and resolving any database integrity issues before upgrading.
    • Documenting SQL logins, SQL Agent jobs, linked servers, credentials, certificates, service accounts, Database Mail settings, and application connection details.
    • Preparing and testing a rollback or recovery plan. A VM snapshot should not be considered a substitute for SQL Server backups.
    • Testing the complete upgrade process in a non-production environment whenever possible.
    • Confirming that neither Windows nor SQL Server has a pending restart before beginning the upgrade.

    Some of the main risks to consider include:

    • Application or driver compatibility issues.
    • Query plan or performance changes after the SQL Server upgrade.
    • Deprecated or discontinued SQL Server features.
    • Issues with SQL Server services, Agent jobs, linked servers, SSIS packages, or third-party monitoring and backup tools.
    • Extended downtime or challenges during rollback if an in-place upgrade does not complete successfully.
    • Availability Group, clustering, or replication-related issues in high-availability environments.
    • Operating system, storage, network, antivirus, or hardware driver compatibility concerns during the Windows Server upgrade.

    For business-critical production environments, a side-by-side migration to a new Windows Server 2022 server running SQL Server 2022 is often the safest approach. Although it requires additional planning and infrastructure, it provides more flexibility for testing and a much simpler rollback strategy if unexpected issues arise.

    Finally, if this server participates in a SQL cluster, an Availability Group deployment, or hosts another Microsoft workload such as Configuration Manager, Exchange, or a third-party application, be sure to review the product-specific support matrix and upgrade guidance before proceeding.

    I hope this helps clarify the recommended upgrade order and considerations.

    References:

    Version Requirements for SQL Server in Windows Operating System - SQL Server | Microsoft Learn

    Supported Version and Edition Upgrades (SQL Server 2022) - SQL Server | Microsoft Learn

    Plan Your Windows Server Upgrade Path | Microsoft Learn

    Choose a Database Engine Upgrade Method - SQL Server | Microsoft Learn

    Upgrade SQL Server - SQL Server | Microsoft Learn

    In-place change of SQL Server edition - SQL Server | Microsoft Learn

    SQL Server 2022 Release Notes - SQL Server | Microsoft Learn

    If you find it useful, please click Accept Answer.

    Thank you for choosing Microsoft Q&A.

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