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I haven't been able to clearly find an example solving a problem that is exactly like this, so I'm posting this request for help. Ideally, diagnosis of what's wrong with my ecosystem and applicable fixes.

What I'm trying to achieve is have a one machine connect twice to my server, getting two IPs within the VPN's IP pool. The pitfall I'm encountering is that the client with the two IPs only responds on one of those IPs externally. At this point, I'm not even sure this kind of system is supported by OpenVPN.

Here's a brief outline of what's happening... followed by the config files found on the 3 machines.

10.24.10.1 = server (machine 1)
10.24.10.6 = client_a (machine 2)
10.24.10.18 = client_b0 (machine 3)
10.24.10.22 = client_b1 (machine 3)

From within server, or client_a, only one of these will work, the other will fail:

$ ping 10.24.10.18
$ ping 10.24.10.22

From within client_b0 / client_b1, both of these will work:

$ ping 10.24.10.18
$ ping 10.24.10.22

server

server 10.24.10.0 255.255.255.0
port 1194
proto udp
dev tun
ca keys/ca.crt
cert keys/example.com.crt
key keys/example.com.key
dh keys/dh1024.pem
ifconfig-pool-persist ipp.txt
client-to-client
keepalive 10 120
comp-lzo
persist-key
persist-tun
status openvpn-status.log
verb 3

client_a

client
dev tun
proto udp
remote example.com 1194
resolv-retry infinite
nobind
persist-key
persist-tun
ca keys/ca.crt
cert keys/client_a.crt
key keys/client_a.key
ns-cert-type server
comp-lzo
verb 3

client_b0

client
dev tun
proto udp
remote example.com 1194
resolv-retry infinite
nobind
persist-key
persist-tun
ca keys/ca.crt
cert keys/client_b0.crt
key keys/client_b0.key
ns-cert-type server
comp-lzo
verb 3

client_b1

client
dev tun
proto udp
remote example.com 1194
resolv-retry infinite
nobind
persist-key
persist-tun
ca keys/ca.crt
cert keys/client_b1.crt
key keys/client_b1.key
ns-cert-type server
comp-lzo
verb 3

Routing table on machine #3 (client_b0 / client_b1)

Destination     Gateway         Genmask         Flags Metric Ref    Use Iface
xxx.xxx.xxx.71  yy.yy.yyy.131   255.255.255.255 UGH   0      0        0 eth0
10.24.10.21     *               255.255.255.255 UH    0      0        0 tun1
10.24.10.17     *               255.255.255.255 UH    0      0        0 tun0
yy.yy.yyy.0     *               255.255.255.0   U     0      0        0 eth0
10.24.10.0      10.24.10.21     255.255.255.0   UG    0      0        0 tun1
10.24.10.0      10.24.10.17     255.255.255.0   UG    0      0        0 tun0
default         yy.yy.yyy.131   0.0.0.0         UG    0      0        0 eth0

I tend to think that the present routing table has issues with the 10.24.10.### routing (xxx and yy used to mask IP addresses), in which case this becomes less of an OpenVPN question and more of a "what routing setup will I need?"

Thanks~

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