Introduction

Tailscale is a secure VPN solution built on WireGuard® that allows two Windows computers to connect directly over the Internet without opening ports, configuring firewalls, or exposing Remote Desktop (RDP) to the public Internet.

In this guide, we will connect:

• Windows PC (your home computer)
• Windows VPS or remote Windows server

using Tailscale and then access the remote machine through Remote Desktop (RDP).

Benefits:

• No need to open port 3389.
• No public IP exposure.
• End-to-end encrypted connection.
• Easy setup within a few minutes.
• Works behind NAT, routers, and most firewalls.

By the end of this guide, you will be able to connect to your remote Windows system using:

mstsc → Tailscale IP → Connect

Prerequisites

Before starting, ensure you have:

• A Windows PC.
• A Windows VPS or remote Windows machine.
• Administrator access on both systems.
• Internet connection on both systems.
• A Tailscale account.

Network Diagram

No port forwarding or firewall changes are required.

Step 1 – Install Tailscale on the Windows VPS

1. Download Tailscale:

   https://tailscale.com/download

2. Run the installer as Administrator.
3. Complete the installation.
4. Launch Tailscale.
5. Click Log In.
6. Sign in using your Tailscale account.
7. Wait until the status shows:

Connected

Step 2 – Install Tailscale on Your Windows PC

Repeat the same process on your local Windows computer:

1. Download Tailscale.
2. Install it.
3. Log in using the SAME account used on the VPS.
4. Confirm the device appears in your Tailscale dashboard.

Step 3 – Verify Both Devices Are Online

Open the Tailscale application on both machines.

You should see something similar to:

Home-PC
100.x.x.x

Windows-VPS
100.x.x.x

Each device receives its own private Tailscale IP address.

Example:

Home-PC      100.101.102.103
Windows-VPS  100.105.106.107

Step 4 – Enable Remote Desktop on the VPS

On the Windows VPS:

Open:

Settings
→ System
→ Remote Desktop

Enable:

Remote Desktop = ON

Click Confirm when prompted.

Step 5 – Test Connectivity

From your local PC:

Press:

Windows + R

Type:

cmd

Run:

ping 100.105.106.107

Replace the IP with your VPS Tailscale IP.

Successful replies indicate the VPN tunnel is working.

Step 6 – Connect Using Remote Desktop

Press:

Windows + R

Type:

mstsc

Click OK.

In the Computer field enter:

100.105.106.107

Click Connect.

Enter:

Username: Administrator
Password: Your VPS Password

Click OK.

You should now see the VPS desktop.

Step 7 – Save the RDP Connection (Optional)

Inside Remote Desktop Connection:

1. Click Show Options.
2. Enter the Tailscale IP.
3. Save credentials if desired.
4. Click Save As.

Example:

My-VPS.rdp

Future connections require only a double-click on the saved RDP file.

Troubleshooting

Cannot Connect

Verify:

• Tailscale is running on both devices.
• Both devices are logged into the same Tailscale account.
• Remote Desktop is enabled on the VPS.
• Windows Firewall has not disabled RDP.

Tailscale Connected but RDP Fails

Check that Remote Desktop is enabled:

Settings
→ System
→ Remote Desktop

and ensure the VPS user account has a password.

VPS Appears Offline

Restart Tailscale from:

System Tray
→ Right Click Tailscale
→ Disconnect
→ Connect

or reboot the VPS.

Conclusion

Tailscale provides a simple and secure way to access a Windows VPS or remote Windows computer through Remote Desktop without exposing RDP to the public Internet. Once installed on both devices, you can connect using the private Tailscale IP address, eliminating the need for port forwarding, VPN servers, or complex firewall configurations.

For most users, the entire setup takes less than 10 minutes and significantly improves the security of Windows Remote Desktop access.