@marvosa:
Need to clarify some info:
Your diagram shows "OpenVPN Tunnel Network: 10.0.10.0/24" and "Subnet to pfSense3: 10.0.10.8/30". Please clarify what you meant because those networks overlap.
When you say "I have a remote site connected with OpenVPN Peer to Peer (SSL/TLS) working" you never specified what was connected. I can only assume from your diagram that you meant PFsense 1 and PFsense 3 are connected and that each side can communicate with the other side's LAN, but please verify my assumption is correct.
On PFsense 2, is there a typo or is 172.16.10.1/26 really a WAN interface? Why isn't it a LAN interface? I would imagine 172.16.20.0/26 cannot communicate with 172.16.10.0/26 because there is no return route back to 172.16.20.0/26 on PFsense 2. Although, I'm not even sure that's possible because it's a WAN interface and being NAT'd… someone else chime in if they know for sure
you need a return route to 172.16.20.0/26 on the cisco.
Remember
Post your server1.conf from PFsense 1 and client1.conf from PFsense 3.
pfSense1 Site2Site (PKI)
dev ovpns2
dev-type tun
tun-ipv6
dev-node /dev/tun2
writepid /var/run/openvpn_server2.pid
#user nobody
#group nobody
script-security 3
daemon
keepalive 10 60
ping-timer-rem
persist-tun
persist-key
proto udp
cipher AES-256-CBC
up /usr/local/sbin/ovpn-linkup
down /usr/local/sbin/ovpn-linkdown
local TRIMMED-PUBLIC-IP
tls-server
server 10.0.10.0 255.255.255.0
client-config-dir /var/etc/openvpn-csc
ifconfig 10.0.10.1 10.0.10.2
tls-verify /var/etc/openvpn/server2.tls-verify.php
lport 1195
management /var/etc/openvpn/server2.sock unix
ca /var/etc/openvpn/server2.ca
cert /var/etc/openvpn/server2.cert
key /var/etc/openvpn/server2.key
dh /etc/dh-parameters.1024
tls-auth /var/etc/openvpn/server2.tls-auth 0
route 172.16.20.0 255.255.255.192
route 172.16.20.64 255.255.255.192
route 192.168.0.0 255.255.255.0
push "route 172.16.0.0 255.255.248.0"
push "route 172.16.10.0 255.255.255.192"
push "route 10.2.6.0 255.255.255.0"
push "route 10.2.31.0 255.255.255.0"
push "route 10.31.10.0 255.255.255.0"
push "route 10.31.112.0 255.255.255.0"
push "route 10.31.253.0 255.255.255.0"
push "route 10.32.253.0 255.255.255.0"
push "route 10.252.130.0 255.255.255.0"
push "route 10.252.144.0 255.255.255.0"
push "route 10.252.252.0 255.255.255.0"
push "route 10.253.1.192 255.255.255.255"
push "route 10.253.252.0 255.255.255.0"
pfSense3 (Client)
dev ovpnc1
dev-type tun
dev-node /dev/tun1
writepid /var/run/openvpn_client1.pid
#user nobody
#group nobody
script-security 3
daemon
keepalive 10 60
ping-timer-rem
persist-tun
persist-key
proto udp
cipher AES-256-CBC
up /usr/local/sbin/ovpn-linkup
down /usr/local/sbin/ovpn-linkdown
local TRIMMED-PUBLIC-IP
tls-client
client
lport 0
management /var/etc/openvpn/client1.sock unix
remote TRIMMED-REMOTE-IP 1195
ifconfig 10.0.10.2 10.0.10.1
ca /var/etc/openvpn/client1.ca
cert /var/etc/openvpn/client1.cert
key /var/etc/openvpn/client1.key
tls-auth /var/etc/openvpn/client1.tls-auth 1
Also here is the CSO (-csc) file for that client
ifconfig-push 10.0.10.10 10.0.10.9
iroute 172.16.20.0 255.255.255.192
USING Site2Site
12:00:41.556303 IP 192.168.0.47.38007 > 10.31.10.89.33438: UDP, length 24
12:00:41.628250 IP 192.168.0.47.38007 > 10.31.10.89.33439: UDP, length 24
12:00:41.699052 IP 192.168.0.47.38007 > 10.31.10.89.33440: UDP, length 24
12:00:41.770609 IP 192.168.0.47.38007 > 10.31.10.89.33441: UDP, length 24
12:01:55.579807 IP 192.168.0.47.38022 > 10.31.10.89.33441: UDP, length 24
12:02:00.580990 IP 192.168.0.47.38022 > 10.31.10.89.33442: UDP, length 24
12:02:05.581638 IP 192.168.0.47.38022 > 10.31.10.89.33443: UDP, length 24
12:02:10.582314 IP 192.168.0.47.38022 > 10.31.10.89.33444: UDP, length 24
USING RoadWarrior
11:35:41.019829 IP 10.0.8.202.37905 > 10.31.10.89.33435: UDP, length 24
11:35:41.182282 IP 10.0.8.202.37905 > 10.31.10.89.33436: UDP, length 24
11:35:41.253157 IP 10.0.8.202.37905 > 10.31.10.89.33437: UDP, length 24
11:35:41.324107 IP 10.0.8.202.37905 > 10.31.10.89.33438: UDP, length 24
11:37:07.139149 IP 10.31.253.2.46027 > 10.31.10.89.33438: UDP, length 24
11:37:07.281083 IP 10.31.253.2.15414 > 10.31.10.89.33439: UDP, length 24
11:37:07.351882 IP 10.31.253.2.3381 > 10.31.10.89.33440: UDP, length 24
11:37:07.422730 IP 10.31.253.2.23474 > 10.31.10.89.33441: UDP, length 24