AWS VPN site-to-site tunnel behind NAT using pfSense IKEv1 IPsec VPN protocol

Pre-configuration steps

Desired configuration achieved by this tutorial is presented on below diagram.

Diagram 1 Environment for testing AWS VPN using pfSense
Diagram 1 Environment for testing AWS VPN using pfSense

Workstation environment

For the purpose of presentation AWS VPN capabilities, virtual environment had been created on VMware Workstation 14.

Networking – initial configuration

Our Network configuration is presented in the table:

Name IP address Interface Purpose
Gateway 10.2.0.100/16 pfSense Gateway, ref. pfSense WAN
dc.regmen.com 10.2.0.40/16 local Windows 2008 Domain Controller, DNS server
linux1 10.2.0.50/16 lin_vif Management server
  10.2.0.51/16 eno16777736
pfSense WAN 192.168.1.112/24 WAN
pfSense LAN 10.20.0.100/16 LAN

Table 1 Networking – on-premise. (more…)

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