I found this
http://serverfault.com/questions/593314/openvpn-routing-for-lan-to-lan-through-tun
This is the exact same problem as I'm having so I added the highlighted lines to the server configuration
dev tun
proto udp
port 1194
ca /etc/openvpn/easy-rsa/pki/ca.crt
cert /etc/openvpn/easy-rsa/pki/issued/server.crt
key /etc/openvpn/easy-rsa/pki/private/server.key
dh /etc/openvpn/easy-rsa/pki/dh2048.pem
topology subnet
server 10.8.0.0 255.255.255.0
# server and remote endpoints
ifconfig 10.8.0.1 10.8.0.2
# Add route to Client routing table for the OpenVPN Server
push "route 10.8.0.1 255.255.255.255"
# Add route to Client routing table for the OPenVPN Subnet
push "route 10.8.0.0 255.255.255.0"
# your local subnet
push "route 0.0.0.0"
[b]push "route 169.254.27.0 255.255.255.0"
route 169.254.27.0 255.255.255.0
client-config-dir /etc/openvpn/ccd[/b]
# Set your primary domain name server address for clients
push "dhcp-option DNS 8.8.8.8"
push "dhcp-option DNS 8.8.4.4"
# Override the Client default gateway by using 0.0.0.0/1 and
# 128.0.0.0/1 rather than 0.0.0.0/0. This has the benefit of
# overriding but not wiping out the original default gateway.
#push "redirect-gateway def1"
client-to-client
duplicate-cn
keepalive 10 120
tls-version-min 1.2
tls-auth /etc/openvpn/easy-rsa/pki/ta.key 0
cipher AES-256-CBC
auth SHA256
comp-lzo
user nobody
group nogroup
persist-key
persist-tun
This is what my ccd file looks like
ifconfig-push 10.8.0.101 10.8.0.102
push "route 192.168.2.0 255.255.255.0
iroute 169.254.27.101 255.255.255.0
I tried this
# Masquerade outgoing traffic
iptables -t nat -A POSTROUTING -o eth0 -j MASQUERADE
iptables -t nat -A POSTROUTING -o tun0 -j MASQUERADE
# Allow return traffic
iptables -A INPUT -i eth0 -m state --state RELATED,ESTABLISHED -j ACCEPT
iptables -A INPUT -i tun0 -m state --state RELATED,ESTABLISHED -j ACCEPT
# Forward everything
iptables -A FORWARD -j ACCEPT
I'm still not able to ping 169.254.27.101 from anywhere but the client itself.