The first step in upgrading from SharePoint 2016 to SharePoint 2019 is conducting a thorough assessment of your current environment. Organizations should inventory all content databases, custom solutions, workflows, and third-party integrations. By understanding the scope and complexity of the current setup, businesses can avoid unexpected roadblocks. It’s also crucial to evaluate whether your existing infrastructure meets the hardware and software requirements of SharePoint 2019. Planning should include stakeholder involvement, setting realistic timelines, and defining success metrics for the upgrade.
Before initiating the upgrade, you need to prepare both the SharePoint 2016 environment and the new SharePoint 2019 infrastructure. This involves ensuring that all databases are healthy, clearing out unused content, and applying the latest updates and patches to the SharePoint 2016 farm. Establishing a new SharePoint 2019 farm with appropriate configuration settings and security practices is essential. Make sure the new servers are set up according to Microsoft’s best practices, with the correct roles and services assigned.
The upgrade process from SharePoint 2016 to SharePoint 2019 follows a database attach method. This requires detaching content databases from the SharePoint 2016 farm, backing them up, and restoring them to the SQL Server intended for the SharePoint 2019 environment. Once restored, the databases can be attached to the new SharePoint 2019 farm using PowerShell commands. It’s important to verify that databases are upgraded successfully and that all custom solutions are compatible with SharePoint 2019 before proceeding further.
After the databases have been attached to the new farm, thorough validation and testing must be performed. This step ensures that all content, sites, workflows, and customizations function correctly in SharePoint 2019. Establish a test plan that includes checking site collections, verifying search functionality, and ensuring that user permissions have been migrated accurately. Any issues identified during this phase should be addressed before moving on to full production deployment.
Custom solutions and third-party integrations present significant challenges during the upgrade. Before beginning the database attach process, organizations should verify that all custom features are compatible with SharePoint 2019. Some legacy solutions may need to be redeveloped or replaced with modern alternatives. SharePoint 2019 supports new frameworks such as SharePoint Framework (SPFx), which can enhance user experience and integration capabilities. Close coordination between development and IT teams is necessary to avoid functionality disruptions.
Once validation and testing are complete, the next step is planning and executing the production cutover. Organizations can choose between a phased approach or a complete cutover. A phased approach migrates site collections and content databases in stages, allowing for more control and the ability to resolve issues as they arise. A complete cutover migrates everything in a single event, which can be faster but carries more risk. Whichever method is chosen, communication with end-users and stakeholders is critical to ensure a smooth transition.
After the production environment has been upgraded, monitoring and optimization are essential. Continuous monitoring of system performance, search indexing, and workflow execution ensures that any lingering issues are identified and resolved quickly. User feedback should be gathered and addressed promptly to enhance adoption. Additionally, the post-upgrade phase provides an opportunity to optimize site structures, clean up outdated content, and improve governance policies for future maintenance.
Upgrading to SharePoint 2019 also necessitates a review and update of governance and compliance policies. Organizations should establish clear guidelines for site creation, content management, data retention, and user permissions within the new environment. Compliance with data protection regulations must be reassessed to ensure the organization meets legal and industry standards. Involving compliance officers and security experts in this phase will help mitigate risks and maintain trust.
User adoption plays a vital role in the success of any upgrade. Training programs tailored to different user groups, from site owners to end-users, are essential to help them adapt to the new platform. Training should cover new features, user interfaces, and best practices for content management. Additionally, change management efforts, including regular communication and user support, will help smooth the transition and encourage widespread adoption.
The final stage of the upgrade process is developing a long-term maintenance and upgrade plan. Regular updates, security patching, and system health checks are necessary to keep the environment running smoothly. Organizations should also establish a process for continuous improvement, leveraging the latest features and enhancements offered by SharePoint 2019. This proactive approach ensures that the organization remains agile, secure, and ready for future upgrades to newer SharePoint versions or cloud-based solutions.

Upgrading from SharePoint 2016 to SharePoint 2019 is a multi-phase process that requires meticulous planning, collaboration, and execution. By conducting a thorough assessment, preparing the environment, handling custom solutions effectively, and maintaining clear communication with stakeholders, organizations can complete the transition without significant disruptions. Post-upgrade monitoring, governance updates, and robust training initiatives further contribute to a successful upgrade. With careful preparation and proactive management, businesses can take full advantage of SharePoint 2019’s capabilities, ensuring their digital workspace remains modern, secure, and efficient for years to come.
At Code Creators, we specialize in making SharePoint upgrades seamless and efficient. Our SharePoint migration consulting ensure a smooth transition from SharePoint 2016 to 2019 — minimizing downtime, preserving data integrity, and optimizing your new environment for long-term success. Let our experts handle the complexities so you can focus on driving productivity and growth. Contact us today to start your upgrade journey with confidence!