For decades, traditional on-premises file servers with mapped network drives—such as the familiar Z: or K: drive—were a standard part of corporate IT environments.
However, as hybrid work has become a normal part of business and organizations move more workloads to the cloud, many companies are reconsidering whether they still need traditional file servers for everyday document storage.
As an IT Systems Manager, moving some of our company’s structured departmental data from a traditional file server to SharePoint Online has been one of the more practical cloud migration projects I’ve worked on.
It wasn’t simply a matter of copying folders from a server to the cloud. We had to consider user habits, permissions, file paths, local disk space, remote access, and how employees would actually work with their files after the migration.
Here is what I’ve learned from migrating company files to SharePoint Online, including some of the challenges and practical solutions I’ve encountered along the way.
1. Accessibility: Less Reliance on VPN
One of the biggest differences between a traditional file server and SharePoint Online is how users access their files remotely.
Traditional File Servers
With a traditional on-premises file server, remote employees typically need to connect to the company’s VPN before they can access network drives.
From an IT support perspective, this can create additional work:
- VPN account and access management
- Password and authentication issues
- Troubleshooting dropped VPN connections
- Slow file access over a remote connection
- Users forgetting to connect to the VPN before opening a network drive
When most employees were working from the office, this wasn’t necessarily a major problem.
However, as remote and hybrid work became more common, VPN dependency became much more noticeable.
SharePoint Online
With SharePoint Online, users can access their documents through a web browser, Microsoft Teams, or the OneDrive sync client.
This doesn’t eliminate every access or authentication issue, but it can significantly reduce the dependency on a traditional VPN for everyday document access.
For IT teams, moving suitable file shares to SharePoint can therefore simplify remote access while giving employees a more consistent experience regardless of where they are working.
2. Local Disk Management and Files On-Demand
One concern I had when moving users from a file server to SharePoint was local laptop storage.
When a SharePoint document library is synced through OneDrive, users can see their files directly in Windows File Explorer. However, files that are opened or downloaded can become locally available and consume disk space.
This can become a problem on laptops with relatively small SSDs, especially when users work with large documents, media files, or other data-heavy content.
The Solution: OneDrive Files On-Demand
This is where OneDrive Files On-Demand becomes extremely useful.
Files can remain online-only until users need them. When a user opens an online-only file, it can be downloaded and made available locally.
Windows Storage Sense can also help manage locally available cloud content by automatically making inactive files online-only again.
In Windows 11 version 22H2 and later, the default setting for OneDrive cloud files is to make them online-only if they haven’t been opened for more than 30 days. Administrators can configure a different threshold depending on their organization’s requirements.
My Practical Approach
For environments where laptop storage is a concern, IT can consider a shorter threshold—for example, 15 days—for files that haven’t been accessed recently.
The important point is that this doesn’t delete the files from SharePoint.
It simply removes the local copy and keeps the file available in the cloud.
This can be particularly useful for organizations where employees have large document libraries but don’t need every file stored locally all the time.
3. Bridging the Gap for “Old-School” Users: ZeeDrive
Moving to SharePoint doesn’t automatically mean every employee will be comfortable with the new way of working.
Some users simply prefer the traditional Windows File Explorer experience.
They are used to opening:
Z:\Finance
or:
K:\Shared\Projects
and they don’t want to think about SharePoint sites, document libraries, or browser-based file access.
I’ve found that user adoption is an important part of any file server migration.
The Challenge
OneDrive can synchronize SharePoint libraries into File Explorer, but it isn’t exactly the same as a traditional mapped network drive.
There are also legacy approaches such as WebDAV, but they aren’t generally the solution I would want to rely on for a modern business environment.
Using ZeeDrive
For users who strongly prefer the traditional mapped-drive experience, we use a third-party application called ZeeDrive.
ZeeDrive can map SharePoint Online libraries to standard Windows drive letters without requiring the entire library to be synchronized to the local computer.
For certain users, this provides a familiar interface while keeping the underlying data in SharePoint.
I don’t think every organization needs a mapped-drive solution.
However, in my experience, having a practical option for users who struggle with a completely new workflow can make a migration much smoother.
Technology migrations aren’t only about choosing the technically best platform. User adoption matters just as much.
4. Migration Execution: The SharePoint Migration Tool
Migrating gigabytes—or even terabytes—of file server data to SharePoint is not as simple as dragging folders into a web browser.
For a small amount of data, a browser upload may be fine.
For a real business file server, however, you need a proper migration strategy.
Why I Prefer a Migration Tool
Microsoft provides the SharePoint Migration Tool (SPMT) for migrating content from supported sources, including local and network file shares.
One of the biggest advantages is that you can scan and assess your source data before starting the actual migration.
This gives IT an opportunity to identify problems such as:
- Invalid file or folder names
- Long file paths
- Permission issues
- Unsupported content
- Large or problematic files
- Complicated folder structures
SharePoint Online has a 400-character path limit, so long and deeply nested folder structures should be reviewed before migration.
SPMT can also preserve file-share permissions when configured appropriately, and migration jobs can be rerun incrementally to copy new or updated files after the initial migration.
A Practical Migration Approach
For a larger file server migration, I would generally recommend:
- Review the existing file server structure.
- Identify which data actually needs to move.
- Clean up obsolete or duplicate data.
- Scan the source for migration issues.
- Design the SharePoint sites and document libraries.
- Perform an initial migration.
- Allow users to continue working with the existing file server if necessary.
- Run an incremental migration before the final cutover.
- Confirm permissions and access.
- Switch users to the new SharePoint location.
The goal isn’t simply to move every folder from the old server into SharePoint.
It’s an opportunity to rethink how the organization stores and manages information.
5. Collaboration, Version History and Security
Another major advantage of SharePoint is that it provides capabilities that are difficult to replicate with a traditional file server.
Collaboration
Microsoft 365 applications can support real-time collaboration on supported documents stored in SharePoint.
Instead of sending multiple copies of a Word or Excel file back and forth through email, users can work from the same document.
This can significantly reduce the classic:
“Final.xlsx”
“Final_v2.xlsx”
“Final_v2_REAL_FINAL.xlsx”
problem.
Version History
SharePoint also provides version history, allowing users to view and restore previous versions of files.
This is particularly useful when someone accidentally overwrites or changes a document. Microsoft describes version history as part of the built-in data protection capabilities of SharePoint and OneDrive.
Of course, version history shouldn’t be considered a complete replacement for a proper Microsoft 365 backup strategy.
For business-critical data, I still believe organizations should consider a dedicated backup solution.
External Sharing
SharePoint also provides more controlled options for collaborating with external organizations.
Instead of sending large attachments through email or using consumer file-sharing services, administrators can configure SharePoint and OneDrive external sharing settings according to the organization’s security requirements.
For example, organizations can restrict external sharing at the site level, limit sharing by domain, control guest access, and integrate external collaboration with Microsoft Entra settings.
This gives IT more control over how business documents are shared outside the organization.
What I Would Consider Before Migrating
Based on my experience, I wouldn’t recommend simply asking:
“Can we move our file server to SharePoint?”
Instead, I would ask:
1. Does this data actually need to be migrated?
Old, duplicate, or unused data doesn’t necessarily need to move to the cloud.
2. Who needs access?
Review existing NTFS and share permissions before recreating access in SharePoint.
3. How should the data be organized?
Don’t automatically recreate the exact same folder structure.
SharePoint sites, document libraries, folders, Microsoft 365 groups, and Teams can provide different ways of organizing information.
4. How will users access their files?
Will they use:
- SharePoint in a browser?
- Microsoft Teams?
- OneDrive sync?
- A mapped-drive solution such as ZeeDrive?
The answer may be different for different departments.
5. What happens to the old file server?
Don’t immediately shut down the server after migration.
First confirm that users can access the new location, permissions are correct, important files are present, and business processes are working normally.
Conclusion
Migrating from a traditional file server to SharePoint Online isn’t simply a storage migration.
It’s a change in how employees access, collaborate on, and manage company information.
For our environment, moving appropriate file server data to SharePoint has helped reduce dependence on traditional infrastructure while providing better support for remote access and modern collaboration.
However, the technology itself isn’t the hardest part.
The biggest challenge is often the people.
Some users adapt quickly to SharePoint and OneDrive, while others strongly prefer the familiar mapped-drive experience they’ve used for years.
That’s why I believe a successful migration needs to balance technology, security, and user experience.
Tools such as SharePoint Migration Tool, OneDrive Files On-Demand, and solutions like ZeeDrive can help address different parts of the transition.
And most importantly, don’t treat a file server migration as a simple copy-and-paste project.
Take the opportunity to clean up old data, rethink your folder structure, review permissions, and design the new environment around how the business actually works.
For an IT team, that can turn a routine infrastructure project into a much more valuable modernization project.
If you’re also managing Microsoft 365 or Windows devices, you may find these related articles useful:
- [7 Things I’ve Learned Managing Microsoft 365 in a Real Business Environment] https://aussiekim.com/microsoft-365-management-real-business/
- [Microsoft Intune: How I Manage Company Laptops and Devices] https://aussiekim.com/microsoft-intune-device-management/
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