OpenVPN Connection fails with DNSMasq (pi-hole)
I have a VPS running an OpenVPN server. The VPN works fine before adding pi-hole and rebooting.
I set up the OpenVPN server using this guide: https://www.digitalocean.com/community/tutorials/how-to-set-up-an-openvpn-server-on-ubuntu-16-04
I set up pi-hole with this: https://www.cyberciti.biz/faq/ubuntu-linux-install-pi-hole-with-a-openvpn/
Once I install pi-hole, it works fine. The VPN still works, and I can access the pi-hole admin page from my client connection. But once I reboot the server, and then connect to the VPN, all DNS lookups fail. I also cannot ping an IP from my client while connected to the VPN after the server reboot.
For the life of me I can’t figure out what’s causing the issue. The firewalls seem fine. OpenVPN is pushing the DNS to the local IP.
Before restarting the server, I restarted the firewall and OpenVPN. It still worked then. So I can’t figure out what a server reboot would have done to make the VPN connection fail.
Thanks in advance for your help.
port 443 proto tcp dev tun ca ca.crt cert server.crt key server.key # This file should be kept secret dh dh2048.pem server 10.8.0.0 255.255.255.0 ifconfig-pool-persist ipp.txt push "redirect-gateway def1 bypass-dhcp" push "dhcp-option DNS 10.8.0.1" keepalive 10 120 tls-auth ta.key 0 # This file is secret key-direction 0 cipher AES-128-CBC # AES auth SHA256 comp-lzo user nobody group nogroup persist-key persist-tun
UFW OpenVPN rules
# START OPENVPN RULES # NAT table rules *nat :POSTROUTING ACCEPT [0:0] # Allow traffic from OpenVPN client to eth0 -A POSTROUTING -s 10.8.0.0/8 -o ens3 -j MASQUERADE COMMIT # END OPENVPN RULES