Advanced Setup Guides
OpenVPN over Stunnel

38min
Setting Up OpenVPN over Stunnel on Ubuntu 22.04
Introduction
This guide provides a step-by-step walkthrough on how to set up OpenVPN over Stunnel on Ubuntu 22.04. By encapsulating OpenVPN traffic within an SSL tunnel using Stunnel, you can enhance security and potentially bypass network restrictions or firewalls that block or throttle VPN connections.
Prerequisites
VPS Server:
An EDIS Global VPS running Ubuntu 22.04.
Root or sudo access.
Client Machine:
A computer running Ubuntu or any Linux distribution compatible with OpenVPN and Stunnel.
Root or sudo access.
Overview
We will perform the following high-level steps:
On the VPS Server:
Install and configure Stunnel.
Install and configure OpenVPN.
On the Client Machine:
Install and configure Stunnel.
Configure OpenVPN to connect through Stunnel.
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Steps on the VPS Server
1. Update and Upgrade System Packages
Ensure your system packages are up to date.
Text
sudo apt update && sudo apt upgrade -y
sudo apt update && sudo apt upgrade -y
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Explanation: This updates the package list and upgrades installed packages to their latest versions, ensuring you have the latest security patches and features.
2. Install Stunnel
Install Stunnel, which will be used to create an SSL tunnel for OpenVPN traffic.
Text
sudo apt install stunnel4 -y
sudo apt install stunnel4 -y
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Explanation: Installs the Stunnel package, allowing you to encrypt arbitrary TCP connections inside SSL.
3. Generate SSL Certificates for Stunnel
Navigate to the Stunnel configuration directory and generate a self-signed SSL certificate.
Text
cd /etc/stunnel
sudo openssl req -new -x509 -days 365 -nodes -out stunnel.pem -keyout stunnel.pem
cd /etc/stunnel
sudo openssl req -new -x509 -days 365 -nodes -out stunnel.pem -keyout stunnel.pem
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Explanation:
openssl req -new -x509 -days 365 -nodes: Generates a new X.509 certificate valid for 365 days without a passphrase (-nodes).
-out stunnel.pem -keyout stunnel.pem: Outputs both the certificate and the private key to stunnel.pem.
Note: You'll be prompted to enter information (Country, State, etc.). You can fill these out or leave them blank.
4. Create a Log File for Stunnel
Create a log file for Stunnel to write logs.
Text
sudo mkdir -p /var/log/stunnel
sudo touch /var/log/stunnel/stunnel.log
sudo chown stunnel4:stunnel4 /var/log/stunnel/stunnel.log
sudo mkdir -p /var/log/stunnel
sudo touch /var/log/stunnel/stunnel.log
sudo chown stunnel4:stunnel4 /var/log/stunnel/stunnel.log
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Explanation:
Creates a directory for Stunnel logs.
Creates an empty log file and sets appropriate ownership.
5. Configure Stunnel
Open the Stunnel configuration file.
Text
sudo nano /etc/stunnel/stunnel.conf
sudo nano /etc/stunnel/stunnel.conf
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Add the following configuration:
Text
# Global options
output = /var/log/stunnel/stunnel.log

# Service-level options
[openvpn]
client = no
accept = 443
connect = 127.0.0.1:1194
cert = /etc/stunnel/stunnel.pem
# Global options
output = /var/log/stunnel/stunnel.log

# Service-level options
[openvpn]
client = no
accept = 443
connect = 127.0.0.1:1194
cert = /etc/stunnel/stunnel.pem
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Explanation:
output: Specifies where to write log output.
[openvpn]: Defines a service named "openvpn".
client = no: Runs Stunnel in server mode.
accept = 443: Listens on port 443 (common HTTPS port, often allowed through firewalls).
connect = 127.0.0.1:1194: Forwards incoming connections to the local OpenVPN service.
cert: Specifies the SSL certificate file.
6. Enable and Start Stunnel Service
Enable Stunnel to start on boot and start the service.
Text
sudo systemctl enable stunnel4
sudo systemctl restart stunnel4
sudo systemctl status stunnel4
sudo systemctl enable stunnel4
sudo systemctl restart stunnel4
sudo systemctl status stunnel4
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Explanation:
enable: Ensures Stunnel starts on system boot.
restart: Starts or restarts the Stunnel service.
status: Checks if Stunnel is running correctly.
7. Install OpenVPN
Download and run the OpenVPN installation script.
Text
cd ~
wget https://git.io/vpn -O openvpn-install.sh
sudo bash openvpn-install.sh
cd ~
wget https://git.io/vpn -O openvpn-install.sh
sudo bash openvpn-install.sh
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Explanation: This script automates OpenVPN installation and configuration. It will prompt for configuration options—choose settings that suit your needs.
8. Modify OpenVPN Server Configuration
Edit the OpenVPN server configuration file to listen on all interfaces.
Text
sudo nano /etc/openvpn/server/server.conf
sudo nano /etc/openvpn/server/server.conf
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Find and modify the local directive:
Text
# Comment out if present:
# local 127.0.0.1

# Or add:
local 0.0.0.0
# Comment out if present:
# local 127.0.0.1

# Or add:
local 0.0.0.0
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Explanation: Setting local 0.0.0.0 ensures OpenVPN listens on all network interfaces.
9. Restart OpenVPN Service
Apply the configuration changes.
Text
sudo systemctl restart openvpn-server@server.service
sudo systemctl status openvpn-server@server.service
sudo systemctl restart openvpn-server@server.service
sudo systemctl status openvpn-server@server.service
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Explanation: Restarts the OpenVPN service and verifies it's running properly.
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Steps on the Client Machine
1. Install Stunnel
Install Stunnel on the client machine.
Text
sudo apt install stunnel4 -y
sudo apt install stunnel4 -y
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2. Configure Stunnel
Navigate to the Stunnel configuration directory and create the configuration file.
Text
cd /etc/stunnel
sudo nano stunnel.conf
cd /etc/stunnel
sudo nano stunnel.conf
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Add the following configuration:
Text
client = yes

[openvpn]
accept = 127.0.0.1:1194
connect = VPS_IP_ADDRESS:443
client = yes

[openvpn]
accept = 127.0.0.1:1194
connect = VPS_IP_ADDRESS:443
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Explanation:
client = yes: Runs Stunnel in client mode.
accept = 127.0.0.1:1194: Listens locally on port 1194.
connect = VPS_IP_ADDRESS:443: Connects to the VPS server's Stunnel service.
Note: Replace VPS_IP_ADDRESS with your actual VPS server IP.
3. Enable and Start Stunnel Service
Enable Stunnel to start on boot and start the service.
Text
sudo systemctl enable stunnel4
sudo systemctl restart stunnel4
sudo systemctl status stunnel4
sudo systemctl enable stunnel4
sudo systemctl restart stunnel4
sudo systemctl status stunnel4
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4. Copy OpenVPN Client Configuration File
Securely copy the OpenVPN client configuration file from the VPS to your client machine.
Text
scp root@VPS_IP_ADDRESS:/root/client.ovpn ~/
scp root@VPS_IP_ADDRESS:/root/client.ovpn ~/
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Explanation: Copies client.ovpn to your home directory.
Note: Replace VPS_IP_ADDRESS with your VPS IP.
5. Modify OpenVPN Client Configuration
Rename and edit the OpenVPN client configuration file.
Text
sudo mv ~/client.ovpn /etc/openvpn/client.conf
sudo nano /etc/openvpn/client.conf
sudo mv ~/client.ovpn /etc/openvpn/client.conf
sudo nano /etc/openvpn/client.conf
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Modify the following:
Change the remote directive to point to the local Stunnel endpoint:
Add or modify the following directives:
Optionally, specify a log file:
Explanation:
remote 127.0.0.1 1194: Connects OpenVPN to the local Stunnel service.
route-nopull: Prevents automatic route changes.
script-security 2: Allows the execution of scripts.
route-up: Executes a script after connection is established.
6. Create a Routing Script
Create a script to adjust routing after connecting.
Text
sudo nano /etc/openvpn/routing.sh
sudo nano /etc/openvpn/routing.sh
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Add the following content:
Text
#!/bin/bash

SERVER_IP="VPS_IP_ADDRESS"
GATEWAY=$(ip route get 8.8.8.8 | grep -oP 'via \K\S+')
sudo ip route add $SERVER_IP/32 via $GATEWAY
sudo ip route add 0.0.0.0/1 via 10.8.0.1
sudo ip route add 128.0.0.0/1 via 10.8.0.1
#!/bin/bash

SERVER_IP="VPS_IP_ADDRESS"
GATEWAY=$(ip route get 8.8.8.8 | grep -oP 'via \K\S+')
sudo ip route add $SERVER_IP/32 via $GATEWAY
sudo ip route add 0.0.0.0/1 via 10.8.0.1
sudo ip route add 128.0.0.0/1 via 10.8.0.1
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Explanation:
SERVER_IP: Your VPS server IP.
GATEWAY: Determines the default gateway to route traffic to the VPS server outside the VPN tunnel.
The ip route add commands adjust the routing table.
Note: Replace VPS_IP_ADDRESS with your VPS IP.
Make the script executable:
Text
sudo chmod +x /etc/openvpn/routing.sh
sudo chmod +x /etc/openvpn/routing.sh
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7. Start OpenVPN Client
Start the OpenVPN client service.
Text
sudo systemctl enable openvpn-client@client.service
sudo systemctl start openvpn-client@client.service
sudo systemctl status openvpn-client@client.service
sudo systemctl enable openvpn-client@client.service
sudo systemctl start openvpn-client@client.service
sudo systemctl status openvpn-client@client.service
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Explanation: Enables and starts the OpenVPN client using the modified configuration.
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Verification
1. Check IP Address
Before and after starting the VPN, check your public IP to ensure traffic is routed through the VPN.
Text
curl ifconfig.me
curl ifconfig.me
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2. Verify Services
Check that Stunnel and OpenVPN services are running.
Text
sudo systemctl status stunnel4
sudo systemctl status openvpn-client@client.service
sudo systemctl status stunnel4
sudo systemctl status openvpn-client@client.service
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3. Test Connectivity
Ensure you can access internet resources and that traffic is routed through the VPN.
Text
ping -c 4 google.com
traceroute google.com
ping -c 4 google.com
traceroute google.com
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Troubleshooting
Stunnel Connection Refused:
Ensure the VPS firewall allows incoming connections on port 443.
Verify Stunnel is running on the VPS: sudo systemctl status stunnel4.
OpenVPN Authentication Failed:
Check that client and server certificates match.
Review OpenVPN logs on both client and server for errors.
Routing Issues:
Verify the routing.sh script has the correct server IP.
Ensure the script is executable and the path is correct in the OpenVPN config.
Service Fails to Start:
Review logs: journalctl -xe or specific service logs.
Check for typos or syntax errors in configuration files.
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Conclusion
By following this guide, you've successfully set up OpenVPN over Stunnel on Ubuntu 22.04. This configuration provides an additional layer of encryption and can help bypass network restrictions by encapsulating VPN traffic within standard SSL/TLS protocols.
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References
﻿Stunnel Official Documentation﻿
﻿OpenVPN Official Documentation﻿
﻿Ubuntu Server Guide﻿
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Note: Always ensure that your use of VPNs and encryption complies with local laws and regulations.
Updated 13 Sep 2024
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