OpenVPN – Route traffic through openVPN server that is also a client of another openVPN server

I've got an openVPN client connected to an openVPN server with a particular set of routing tables. That openVPN server is also a client connected to another openVPN server with a different set of routing tables. I am having trouble getting my client to route a particular subnet to the second openVPN server.

Here's a quick (and hopefully helpful) illustration of my setup with said routing tables:

draw.io diagram

Client's openvpn client config:

    client
    dev tun0
    proto udp
    remote some-domain.com 1195
    resolv-retry infinite
    nobind
    persist-key
    persist-tun
    comp-lzo
    verb 3
    key keys/vpn192-168-128-0.key
    cert keys/vpn192-168-128-0.crt
    ca keys/ca.crt
    log /var/log/openvpn.log
    verb 4        

    route 10.100.0.0 255.255.255.0
    route 10.55.128.0 255.255.255.0

Server 1's openvpn server config:

    mode server
    tls-server
    port 1195
    proto udp
    dev tun1
    ca server/keys/ca.crt
    cert server/keys/server.crt
    key server/keys/server.key
    dh server/keys/dh1024.pem
    server 10.100.1.0 255.255.255.0
    ifconfig-pool-persist ipp.txt
    topology p2p        

    # route these networks
    route 192.168.128.0 255.255.240.0
    route 10.55.128.0 255.255.255.0      

    client-to-client        

    # client specific configs in here
    client-config-dir ccd
    keepalive 10 120
    comp-lzo
    persist-key
    persist-tun
    status openvpn-status-vpn100.log
    log /var/log/openvpn-server.log
    verb 4

Server 1's client config to Server 2:

    client
    dev tun0
    proto udp
    remote some-domain2.com 1194
    resolv-retry infinite
    nobind
    persist-key
    persist-tun
    comp-lzo
    verb 3
    key /etc/openvpn/client/vpc10-100-0-0.key
    cert /etc/openvpn/client/vpc10-100-0-0.crt
    ca /etc/openvpn/client/ca.crt
    log /var/log/openvpn-client.log
    verb 4
    route 10.55.128.0 255.255.255.128

Server 2's openvpn server config:

    mode server
    tls-server
    port 1194
    proto udp
    dev tun1
    ca keys-vpc/ca.crt
    cert keys-vpc/server.crt
    key keys-vpc/server.key
    dh keys-vpc/dh1024.pem
    server 10.41.88.0 255.255.255.0
    ifconfig-pool-persist ipp.txt
    topology p2p        

    # push 10.45.0.0 route to all connecting clients.
    push "route 10.45.0.0 255.255.128.0"
    push "route 10.39.88.0 255.255.255.0"
    route 10.44.0.0 255.255.128.0 #core-west
    route 10.55.128.0 255.255.128.0 #us-east-1 galaxy
    route 10.100.0.0 255.255.255.0 #gcp-us-east-1
    route 192.168.128.0 255.255.240.0 #gcp-zing-preview        

    client-to-client        

    # client specific configs in here
    client-config-dir ccd-vpc
    keepalive 10 120
    comp-lzo
    persist-key
    persist-tun
    status openvpn-status-vpc.log
    log  /var/log/openvpn-vpc.log
    verb 4
    duplicate-cn

Client's route table:

    default via 192.168.128.1 dev ens4 proto dhcp metric 100
    10.55.128.0/24 via 10.100.1.1 dev tun0
    10.100.0.0/24 via 10.100.1.1 dev tun0
    10.100.1.1 dev tun0 proto kernel scope link src 10.100.1.4
    192.168.128.1 dev ens4 proto dhcp scope link metric 100

Server 1's route table:

    default via 10.100.0.1 dev ens4 proto dhcp metric 100
    10.39.88.0/24 via 10.41.88.1 dev tun0
    10.41.88.0/24 via 10.41.88.1 dev tun0
    10.41.88.1 dev tun0 proto kernel scope link src 10.41.88.6
    10.55.128.0/24 via 10.41.88.1 dev tun0
    10.100.0.1 dev ens4 proto dhcp scope link metric 100
    10.100.1.0/24 via 10.100.1.2 dev tun1
    10.100.1.2 dev tun1 proto kernel scope link src 10.100.1.1
    192.168.128.0/20 via 10.100.1.2 dev tun1

Server 2's route table:

    default via 10.45.0.1 dev eth0
    10.39.88.0/24 dev tun0  proto kernel  scope link  src 10.39.88.1
    10.41.88.0/24 via 10.41.88.2 dev tun1
    10.41.88.2 dev tun1  proto kernel  scope link  src 10.41.88.1
    10.45.0.0/27 dev eth0  proto kernel  scope link  src 10.45.0.10
    10.55.128.0/17 via 10.41.88.2 dev tun1
    10.100.0.0/24 via 10.41.88.2 dev tun1
    192.168.128.0/20 via 10.41.88.2 dev tun1

Iptables are clean on all three boxes as of right now.

I am trying to ping 10.55.128.18 from the client and have it route all the way to Server 2. It makes its way to Server 1 and won't route to Server 2. I can ping 10.55.128.18 directly on Server 1 (not from the client).

I've got IP forwarding enabled everywhere and firewall rules are open for ICMP between all three devices.

Anything insight you can provide would be very helpful!

Thanks.