Still relying on SharePoint 2016 and SharePoint 2019? It’s time to get your head in the cloud.
With end-of-life dates fast approaching, now’s the moment for you to rethink how and where your SharePoint environments live, before outdated infrastructure puts your teams’ productivity and security at risk.
Here’s a quick reminder of the dates:
SharePoint Server 2016: Mainstream support ended July 13, 2021; extended support ends July 14, 2026.
SharePoint Server 2019: Mainstream support ended January 9, 2024; extended support ends July 14, 2026.
Of course, cloud migration isn’t an option for all organizations, so if that’s the case, this blog about on-premises solutions is for you.
But if the cloud is where you’re headed. Read on for more.
Why the urgency?
Mainstream support for SharePoint 2016 and SharePoint 2019 has already ended, with extended support ending on July 14, 2026.
Once those dates pass, your organization will no longer receive security updates, bug fixes, or technical support, leaving critical systems exposed to vulnerabilities and compliance gaps.
But that’s not all. Once extended support ends, the other issue is that legacy platforms simply can’t keep pace with today’s cloud-driven Microsoft 365 ecosystem. From Teams integration to Power Platform and Copilot capabilities, on-premises deployments are being left behind.
Why migrate to SharePoint Online?
The business case for migrating to SharePoint Online goes far beyond staying current. It’s about freeing your IT team from maintenance overheads, improving collaboration, and building a more resilient digital workplace.
Here’s what you can expect:
1. Continuously updated
SharePoint Online is always current, with security patches, performance improvements, and feature enhancements rolled out automatically. So, no more waiting for the next big version release or planning another costly upgrade cycle.
2. A modern experience for a modern workforce
The cloud version delivers a faster, more user-friendly interface across desktop and mobile, designed for modern work. Pages load more quickly, navigation is simpler, and accessibility is built in.
3. Seamless integration with Microsoft 365
SharePoint Online sits at the heart of the Microsoft 365 ecosystem, connecting natively with Teams, Viva, OneDrive, and Power Platform. This means users can move between tools without friction.
4. Reduced operational overheads
Migrating to the cloud means there’s no need for server patching, hardware scaling, and downtime planning, leaving you to focus on strategy and governance instead of firefighting infrastructure issues.
5. Built-in Compliance and Control
SharePoint Online brings your data into Microsoft 365’s unified compliance framework. Features like Data Loss Prevention (DLP), sensitivity labels, and retention policies are built in and automatically updated. That way you’ll be secure and compliant without the manual overhead of on-premises management.
Migration Options for SharePoint 2016/2019 Users
Depending on your timescales, the complexity of your migration or industry requirements, there are three main options available.
1. Lift and Shift
If speed is your priority, a lift-and-shift approach moves your existing SharePoint sites, libraries, and permissions to SharePoint Online as they are.
This might be the quickest way to migrate and involves minimal user disruption, but it also brings legacy design and technical debt with it.
2. Restructured migration
If you’re going to migrate to a new platform, you may as well make some improvements while you’re at it, right?
So, if your organization is looking beyond a simple move, restructured migration means modernizing, reorganizing and redesigning your SharePoint environment to take advantage of modern features like hub sites, improved search, and integration with Teams and Viva.
While this option takes longer it also delivers a far better user experience and aligns your environment with Microsoft 365’s latest capabilities.
3. Hybrid Approach
Not all organizations can go fully cloud-based. For many, regulatory, compliance or security issues mean a hybrid model offers the best of both worlds.
You can move some workloads, like collaboration and communication sites, to SharePoint Online, while keeping sensitive or business-critical data on-premises.
How to Ensure a Smooth Migration
Migrating from SharePoint 2016 or 2019 to SharePoint Online is a major opportunity to modernize your infrastructure, but it can also be complex, particularly when dealing with large volumes of data or extensive customizations.
Here are some best practices to ensure a smooth, secure, and disruption-free migration.
1. Audit your environment
Start with a full audit of your existing environment. Identify what needs to be migrated, what can be archived, and what should be rebuilt. Map dependencies between sites, workflows, and permissions.
A clear migration roadmap, including timelines, testing, and rollback plans, helps minimize surprises later.
2. Declutter
Before you move anything, take the opportunity to declutter. Remove outdated content, consolidate duplicate libraries, and simplify permissions.
A cleaner environment reduces data transfer time and simplifies post-migration management.
3. Test in batches
Run a pilot migration to validate tools, content mapping, and performance. Testing small batches first helps identify and resolve issues before scaling up.
Use this phase to confirm that user access, metadata, and document versions are preserved.
4. Keep teams informed
User adoption is key to success for any tech deployment. Keep teams informed throughout the process. Make sure they know what’s changing, when, and why.
Providing quick-start guides, training, and Q&A sessions can go a long way to help employees adapt to modern SharePoint features and workflows.
5. Validate and Optimize
Once migration is complete, perform post-migration validation to confirm all content, permissions, and workflows have transferred correctly.
Monitor performance and storage, enforce governance policies, and gather feedback to fine-tune the experience.
FAQs on migrating to SharePoint Online
Q: How long does a typical SharePoint migration take?
A: It depends on the size and complexity of your environment. Smaller migrations with limited sites can take a few weeks, while large enterprise environments may require several months. A phased or hybrid approach can help minimize disruption during the transition.
Q: Will all my customizations and workflows carry over automatically?
A: Not necessarily. Custom web parts often need to be rebuilt using modern frameworks such as Power Automate, Power Apps, or SPFx (SharePoint Framework). Reviewing and modernizing these components ahead of migration prevents functionality gaps.
Q: How can I prevent downtime or user disruption during migration?
A: Plan for a phased migration and run pilot tests on low-risk sites first. Communicate timelines clearly to users and schedule final cutovers during off-peak hours. Incremental migration helps maintain access while data is being moved.
Q: Is SharePoint Online secure enough for regulated industries?
A: Yes. SharePoint Online benefits from Microsoft 365’s enterprise-grade security, including encryption, DLP, retention policies, and compliance management through Microsoft Purview. These features are continuously updated to meet evolving industry and regulatory standards.
Q: What happens to my data after migration?
A: All migrated data is stored securely in Microsoft’s cloud under your tenant. Permissions, metadata, and version history can be preserved if configured correctly during migration. Afterward, you can enforce governance and lifecycle policies to ensure data remains compliant.
Q: Do I need additional licensing for SharePoint Online?
A: SharePoint Online is included with most Microsoft 365 business and enterprise plans. However, advanced compliance or Copilot capabilities may require additional licensing.
How Cloudwell can help
Migrating from SharePoint 2016 and 2019 to SharePoint Online isn’t just a technical upgrade, it’s a chance to modernize how your organization works, communicates, and collaborates.
But successful migration takes time, planning, and the right expertise.
Cloudwell’s team has guided enterprise organizations through complex migrations, from full cloud transitions to hybrid deployments, helping them modernize securely and without disruption.
We understand the pressures that come with end-of-life deadlines, creating migration strategies that balance agility, governance, and performance.
Whether you’re looking to streamline collaboration, reduce technical debt, or prepare for AI-driven productivity, we’ll guide you there smoothly.
Talk to our team about your SharePoint migration strategy.