Whether you're uploading a website, deploying an application, or downloading a backup, this guide covers the most reliable methods for transferring files to and from a Windows Server VPS.
Method 1 — Copy/Paste Through RDP (Simplest, Small Files)
Most RDP clients support clipboard file sharing between your local machine and the remote server:
- Copy a file/folder on your local machine (
Ctrl+C) - Switch to the RDP session
- Paste (
Ctrl+V) into the desired location
If this doesn't work, confirm clipboard sharing is enabled in your RDP client's local resources settings before connecting.
Method 2 — Mapping a Local Drive Through RDP
In the Remote Desktop Connection client, before connecting: Show Options → Local Resources → More → check the local drive(s) you want accessible. Once connected, your local drive appears in File Explorer on the remote server under "This PC," letting you drag and drop files directly.
Method 3 — SFTP (Best for Larger/Automated Transfers)
Windows Server can run an SFTP server via OpenSSH, included as an optional Windows feature:
Add-WindowsCapability -Online -Name OpenSSH.Server~~~~0.0.1.0
Start-Service sshd
Set-Service -Name sshd -StartupType 'Automatic'Allow the firewall port:
New-NetFirewallRule -DisplayName "OpenSSH SSH Server" -Direction Inbound -Protocol TCP -LocalPort 22 -Action AllowConnect from your local machine using any SFTP client (FileZilla, WinSCP) or command line:
sftp Administrator@YOUR_SERVER_IPMethod 4 — Robocopy for Bulk/Scripted Transfers Within a Network
For transferring between two Windows machines on the same network:
robocopy C:\LocalFolder \\REMOTE_SERVER\SharedFolder /E /ZMethod 5 — Web-Based Upload (For a Single File, No Client Needed)
If IIS is already running, temporarily host a simple upload page, or use a cloud storage service's web interface to download the file directly onto the server via a browser inside the RDP session.
Which Method Should You Use?
| Scenario | Best Method |
|---|---|
| A few small files, one-off | RDP clipboard copy/paste |
| Large folder, one-off | Mapped local drive through RDP |
| Automated/scripted deployments | SFTP |
| Syncing between two Windows servers | Robocopy |
Common Errors
Clipboard paste doesn't work — local resources/clipboard sharing wasn't enabled before connecting; reconnect with the correct RDP client setting checked.
SFTP connection refused — confirm the sshd service is running and port 22 is allowed in Windows Firewall.
Best Practices
- Use SFTP for automated or scripted deployment workflows
- Never disable encryption/security features just to simplify a one-off transfer
- Verify file integrity after large transfers (compare file sizes or checksums)
Related Articles
- How to Connect to a Windows VPS via Remote Desktop (RDP)
- How to Deploy an ASP.NET Application on IIS
- How to Configure Windows Firewall on a Windows VPS
