Community Insights: Experiences Migrating from SharePoint 2016 to 2019

Why Community Insights Matter for SharePoint Migrations?

Migrating from SharePoint 2016 to 2019 is a major undertaking for any organization, requiring careful planning and execution. While Microsoft provides official guidance, the most valuable lessons often come from the experiences of other organizations that have gone through the process. These community-driven insights shed light on unexpected challenges, clever solutions, and practical advice that can’t be found in documentation alone. In this article, we’ve compiled experiences and tips from the SharePoint community to help others plan and execute smoother migrations, avoid pitfalls, and make the most of their new SharePoint 2019 environment.

The Initial Hesitation: Understanding Why Organizations Wait to Migrate

Many organizations in the SharePoint community admit they delayed migration longer than planned. Common reasons included fear of breaking business-critical custom solutions, concerns about downtime, and worries over user adoption challenges. Several IT leaders shared that internal discussions revolved around the question of whether to move to SharePoint 2019 or jump directly to SharePoint Online. Ultimately, most community members agreed that upgrading to SharePoint 2019 was necessary for those not yet ready for full cloud adoption, thanks to its modern features and enhanced hybrid capabilities.

Pre-Migration Lessons: The Importance of a Clean and Documented Environment

One repeated piece of advice from community members is to spend significant time cleaning up the existing SharePoint 2016 environment before migrating. Organizations that tried to migrate outdated sites, inactive content, and broken workflows faced greater complications. Those who performed thorough content audits, removed obsolete solutions, and documented custom features experienced much smoother transitions. One IT manager shared that they reduced their migration footprint by 40 percent after a proper audit, resulting in faster upgrades and fewer post-migration issues. Documenting all site collections, permissions, workflows, and custom solutions ahead of time was also emphasized as critical for success.

Staging Environments: A Must-Have for Testing and Confidence

The SharePoint community widely agrees that testing in a dedicated staging environment is non-negotiable. Several professionals shared stories of skipped testing leading to broken custom features in production environments, which delayed the entire project and frustrated stakeholders. One consultant highlighted that setting up a staging farm allowed their team to run trial database attaches and test custom solutions before touching the production environment. This step also gave leadership confidence that the project was under control. In addition, staging environments allowed for dry runs of the SharePoint configuration wizard, reducing anxiety about missteps during the real cutover.

Handling Custom Solutions: A Common Roadblock That Requires Early Attention

Custom solutions and third-party tools consistently emerged as the most challenging aspect of migrations. Several organizations underestimated the time needed to redevelop or replace older farm solutions incompatible with SharePoint 2019. Community experts advised starting compatibility checks early in the planning phase. One IT leader shared that their team created an internal “custom solution compatibility matrix” where each solution was marked as compatible, replaceable, or requiring redevelopment. This strategy not only prevented last-minute surprises but also provided clarity to stakeholders who needed to make decisions about legacy tools. For customizations that couldn’t be updated easily, teams turned to SharePoint Framework (SPFx) as a modern alternative with long-term support.

Dealing with Downtime: Managing Stakeholder Expectations

A common challenge reported by community members was managing downtime expectations. Despite the possibility of phased migrations, some downtime is inevitable. Organizations that communicated proactively and set realistic timelines earned greater trust from end-users. One IT department created weekly update emails to stakeholders, highlighting progress and upcoming downtime schedules. Another company shared that they staged cutovers during extended weekend maintenance windows and provided alternative documentation access in case of emergency needs. Overcommunicating the migration timeline, risks, and contingencies proved to be a key success factor according to many community professionals.

Post-Migration Surprises: What Organizations Didn’t See Coming

Even with thorough planning, several organizations encountered surprises post-migration. Some reported unexpected search service issues where indexing failed to function correctly after database attaches. Others found that workflows created in legacy SharePoint Designer required reconfiguration or complete redesign. A recurring theme in community discussions was the difficulty of migrating and validating user permissions. Many organizations faced challenges ensuring that permissions transferred correctly, particularly in complex site collections with multiple owners. The best solutions came from those who included permission mapping and verification in their testing phase and used scripts to compare permissions between source and destination farms.

Optimizing the New Environment: Post-Migration Best Practices

Several IT teams emphasized that post-migration is not the end of the journey but rather the beginning of optimization. Community insights pointed to the importance of running health checks, search re-indexing, and performance tuning in the weeks following the migration. One organization found that their custom branding elements needed adjustments to function properly with modern pages. Another team took advantage of the migration opportunity to standardize content types and metadata structures that had become inconsistent in their previous setup. Investing time in post-migration governance, cleanup, and optimization proved to be essential to achieving the long-term benefits of SharePoint 2019.

User Training and Change Management: Often Overlooked but Crucial

Several community members admitted they underestimated the amount of user training and support needed post-migration. While SharePoint 2019’s interface is more modern and user-friendly, the changes still required explanation, especially for less tech-savvy teams. Organizations that provided structured training sessions, video tutorials, and dedicated support lines experienced smoother adoption. One company held “Ask IT” open hours where users could bring their questions or report issues directly to SharePoint administrators. Another team created quick-reference guides highlighting new features and navigation tips, distributed company-wide during the migration week. Investing in user enablement helped reduce resistance and support tickets.

Reflections on Unexpected Wins

Interestingly, several community stories included unexpected wins. Some organizations found that migrating to SharePoint 2019 prompted greater collaboration between IT and business units, leading to improved communication and faster project cycles for other initiatives. Others discovered that shedding legacy custom solutions encouraged adoption of more standardized features, reducing long-term maintenance burdens. Several companies reported that, after initially resisting the change, end-users appreciated the modern interface and mobile-friendly capabilities of SharePoint 2019. These positive outcomes often emerged after the initial post-migration turbulence had settled.

Advice for Organizations Preparing to Migrate

The strongest advice echoed by the SharePoint community was to avoid rushing. Organizations that took their time to plan, test, and communicate fared much better than those pressured by arbitrary deadlines. Starting with a comprehensive environment audit, building a staging farm, involving key business stakeholders, and dedicating resources to user support were consistent recommendations. Several IT leaders suggested conducting “lessons learned” reviews at each project milestone to improve processes as the migration progressed. Lastly, community members encouraged others to lean on Microsoft’s support resources and user communities, which proved invaluable during unexpected challenges.

Conclusion: Learning from the SharePoint Community for Migration Success

Migrating from SharePoint 2016 to SharePoint 2019 is a complex journey with many moving parts. Community insights reveal that preparation, testing, and clear communication are the cornerstones of success. Challenges with custom solutions, permissions, and downtime are common, but proactive planning and stakeholder engagement help mitigate these issues. Post-migration optimization and user training ensure that the new environment reaches its full potential. By learning from the experiences and practical wisdom of the SharePoint community, organizations can approach their migration projects with greater confidence, efficiency, and long-term success.

At Code Creators, we specialize in helping organizations plan and execute seamless SharePoint migrations. With deep technical expertise and a strong focus on business continuity, our team of SharePoint migration consultants ensures that every step—from initial audits to post-migration optimization—is handled with precision and care. If you’re preparing for a move to SharePoint 2019 or beyond, let our experts guide you toward a smooth, successful transition.