I have the following setup

Site A
10.200.250.0/24 IPSEC VPNed to 10.176.0.0/13

Site B
10.200.240.0/21 OpenVPNed to Site A @ 10.200.250.0/24

I have the following tunnels on OpenVPN on the client side

route 10.176.0.0 255.248.0.0;
route 10.200.240.0 255.255.248.0;

The PFsense can ping IPs on 10.176.0.0 (the one at 10.200.240.x) but machines behind the pfsense cannot.

Can anyone explain?