Win Server Routing

linfante

I tried so many different things for days and I've hit the wall hard. Created my OpenVPN server using the Windows x64 installer in AWS using Server 2016. Created the CA and issued certs no problem with EasyRSA 3. I'm able to connect to OpenVPN with ping and Remote Desktop to the server itself verified as working. I'm unable to get past the server itself to the internal LAN. The server has a public facing IP that is attached to one Network Interface with a DMZ subnet. The other Network Interface is what leads to the rest of the internal network. Any help would be appreciated.

Host - Windows Server 2016
OpenVPN version - 2.5.0
OpenVPN Server IP assigned - 10.0.8.1 (Can ping/RDP from client)
OpenVPN Client IP assigned - 10.0.8.2

AWS Public IP - 52.x.x.x
AWS DMZ subnet (Net Interface 1) - 10.0.55.x

AWS Internal subnet (Net Interface 2) - 10.0.20.x

local 10.0.55.x
port 1194
proto udp
dev tun
ca X.crt
cert X.crt
key X.key
dh X.pem
topology subnet
server 10.0.8.0 255.255.255.0
ifconfig-pool-persist ipp.txt
push "route 10.0.0.0 255.255.0.0"
keepalive 10 120
tls-auth X.key
cipher AES-256-GCM
persist-key
persist-tun
status openvpn-status.log
verb 3
explicit-exit-notify 1

client
dev tun
proto udp
remote 52.x.x.x 1194
resolv-retry infinite
nobind
persist-key
persist-tun
mute-replay-warnings
ca X.crt
cert X.crt
key X.key
remote-cert-tls server
tls-auth X.key 1
cipher AES-256-GCM
verb 3

300000

Going over there get a answer for your lan trouble

https://forums.openvpn.net/viewtopic.php?f=6&t=31230

linfante

You rock. Solved.

I just had to share the connection of my Internal net interface with my TAP. Restarted on both OVPN Server/Client and now I'm able to reach internal networks now.

Thanks

Link below is where I ended up at to figure out what I needed to do.

https://www.reddit.com/r/OpenVPN/comments/81q2q6/guide_how_to_set_up_openvpn_server_on_windows_10/