OneDrive from Windows Server 2025 for remote users

The missing piece is that OneDrive isn’t a background replication service for Windows file shares. An always-on server doesn’t automatically mean OneDrive is running or monitoring the folders your users are editing.

There are two things to check first:

1. Is the OneDrive account actually signed in to Windows? The sync app runs in that user’s session, not as a Windows service. Disconnecting an RDP session normally leaves it running; signing out ends it. After a server restart, it won’t resume just because the server is online—the user session needs to start.
2. Are the shared files actually inside the configured OneDrive folder? OneDrive doesn’t automatically sync other server volumes or SMB shares. Copying files into OneDrive creates a separate copy; later edits to the original share won’t follow. Mapped network drives and junction/symlink workarounds aren’t a supported way to sync an existing file share.

Sign in as the account running OneDrive, check its status and any sync errors, and compare the actual local sync path with the share’s path. Create a small test file directly in the OneDrive folder and check whether it reaches OneDrive on the web. If that works but edits in the server share don’t appear, the folder arrangement is the issue rather than cloud sync speed.

For two people working between office and laptops, a SharePoint document library synced through OneDrive on each computer would usually be a better fit. Migrate the shared business documents there, then have both partners work from that same library instead of maintaining separate live copies on the server and in the cloud.

If the server share must remain the authoritative location, use secure VPN access to it, or evaluate Azure File Sync with Azure Files if you need cloud-backed file-server storage. Azure File Sync does not sync into OneDrive or SharePoint.