PiHole with Recursive DNS not Handshaking with Wireguard setup via PiVPN

If you are experiencing issues with PiHole not handshaking with Wireguard setup via PiVPN, there are a few troubleshooting steps you can take to resolve the problem. This guide will walk you through the process in an easy-to-understand manner.

First, let's understand what PiHole, Wireguard, and PiVPN are:

• PiHole: PiHole is a network-wide ad blocker that acts as a DNS sinkhole. It blocks advertisements at the network level, preventing them from reaching your devices.
• Wireguard: Wireguard is a modern VPN (Virtual Private Network) protocol that provides a secure and fast connection between devices.
• PiVPN: PiVPN is a tool that simplifies the process of setting up a Wireguard VPN on your Raspberry Pi.

Now, let's dive into the troubleshooting steps:

Step 1: Check PiHole Configuration

Ensure that PiHole is correctly configured to listen to the correct network interface. You can do this by following these steps:

1. Access your PiHole admin interface by entering its IP address in a web browser.
2. Go to "Settings" and then "DNS".
3. Under "Interface listening behavior", select "Listen on all interfaces".
4. Click on "Save" to apply the changes.

Step 2: Verify Wireguard Configuration

Make sure that your Wireguard configuration is correct. Check the following:

1. Ensure that the Wireguard server and client configurations are properly set up.
2. Verify that the IP addresses and port numbers in the configurations are correct.
3. Double-check the public keys of the server and client to ensure they match.

Step 3: Check PiVPN Configuration

Verify that PiVPN is correctly configured by following these steps:

1. Access your Raspberry Pi via SSH or directly.
2. Run the command pivpn -d to generate a debug log.
3. Inspect the debug log for any error messages or warnings that could indicate a misconfiguration.

Step 4: Restart Services

If all the configurations appear to be correct, try restarting the necessary services:

1. Restart PiHole by running the command sudo service pihole-FTL restart.
2. Restart Wireguard by running the command sudo systemctl restart wg-quick@wg0.

After restarting the services, check if PiHole and Wireguard are now handshaking properly. If not, continue to the next step.

Step 5: Check Firewall Settings

Ensure that the necessary ports for Wireguard and PiHole are open in your firewall. By default, Wireguard uses UDP port 51820, and PiHole uses TCP/UDP port 53.

Step 6: Seek Further Assistance

If you have followed all the troubleshooting steps and are still experiencing issues, it is recommended to seek further assistance from the PiHole or PiVPN community forums. Provide them with detailed information about your setup and the steps you have already taken.

By following these troubleshooting steps, you should be able to resolve the issue of PiHole not handshaking with Wireguard setup via PiVPN. Remember to double-check your configurations and seek assistance if needed.