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Pretty simple - if I have two WANs, will the site-to-site VPN work if I specify the WAN2 IP address? (It currently works with the WAN1 IP.)

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The answer is No, it will not work.

However, if you set up the correct firewall rules and corresponding static route it is possible to receive IPSec traffic on WAN2, forward to gateway, then static route it out to WAN1.

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