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I'm a bit in over my head with networking issues at the moment. 

 

Device 1: raspberry pi running transmission-daemon and openVPN client connecting to PIA servers. Local IP - 192.168.1.134

Device 2: pfSense box running an openVPN server. VPN traffic binds to 192.168.69.*

Device 3: external device, successfully connected to device 2's openVPN server with a local IP of 192.168.69.6

 

The transmission service running on device 1 has a web GUI accessible at port 9091. The issue is that any device (connected virtually to my local network or not) that is NOT on the 192.168.1.* segment is able to ping device 1, but not access the web GUI on port 9091. I've narrowed things down, and it seems to be solely an issue with what device 1 treats as "local" traffic that doesn't need to be routed through the VPN. 

 

I've tried to use this in my openvpn config file, but things still don't work:

route add 192.168.69.0 mask 255.255.255.0 gw 192.168.1.134"

My complete openvpn config file at the moment:

client
dev tun
proto udp
remote us-east.privateinternetaccess.com 1194
resolv-retry infinite
nobind
persist-key
persist-tun
ca ca.crt
tls-client
remote-cert-tls server
auth-user-pass login.conf
comp-lzo
verb 1
reneg-sec 0
crl-verify crl.pem
auth-nocache

I've also verified that device 3, when connected to the openVPN server of device 2, is able to connect to device 1's web GUI with no problem but only when I disable device 1's VPN client to PIA. Therefore, something about the VPN configuration on device 1 is denying traffic from anything that doesn't share a LAN segment with device 1 (on 191.168.1.*).

 

Any ideas I could try?

CPU: i5 4670k • Cooler: Corsair H100i • Motherboard: MSI Z87 MPOWER • RAM: Crucial Ballistix Elite 2x 8GB • Storage: Samsung 840 250GB SSD, 2x WD Red 3TB • GPU: EVGA GTX 780 3GB • PSU: Corsair RM750W • Case: Corsair 750D • Mouse: Razer Naga 2012 (I actually use the thing for productivity/media buttons) • Keyboard: Ducky Shine 3 w/ Browns - Green LED • Monitor: Asus PB278Q 27" 2560 x 1440, ASUS PB238Q 23" 1920x1080 • Lighting: 2m NZXT Sleeved Blue LED Strip • pcpartpicker.com/p/3cHfZ

 

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