On 06/11/2018 04:55 AM, Mick wrote:
You'll need a trusted gateway to do the unwrapping and then forwarding to the next hop (SSH forwarding). If you attempt TCP-tunneling (TCP-over-TCP) you'll soon experience 'TCP meltdown' with upper and lower TCP layers' retransmission timeouts.

I disagree.

If I can establish an HTTPS (or other TCP connection to carry TLS traffic) out through multiple layers of NAT (SOHO router + CGN + ???) to a server with a globally routed IP address, I should be golden.

NAT will do what it needs to with the internal IPs to establish the connection from the deeply buried client out to the TLS VPN server.

The connection will (extremely likely) be kept alive with various different methods (TCP keep alive or VPN keep alive or pings through the VPN) such that the upstream gateway can send data back to the client through the established VPN.

Arguably this is no different than a long lived HTTP(S) connection from the same client deep behind multiple NATs.

There is no need for something in the middle to unwrap things.

It almost sounds like you're talking about trying to do something from one computer behind one or more NATs to another computer behind one or more NATs on the far end. — That is a far more complex and significantly different problem.

Most corporate VPN users are road warriors and connect from random IPs to a static globally routed IP that is open to the world.

How will you be able to account for such a multi-NAT routing arrangement if (in tunnel rather than transport mode) the original entire IP datagram is encrypted and encapsulated? You'll need to decrypt it, take the payload and read its IP header before you know where to forward it to.

Let me know if my comments above don't answer your question.

On single NAT you encapsulate the IPSec into UDP (NAT-Traversal), but on a double NAT what will you do?

On the second NAT, you pass the UDP traffic from the first NAT.

I've never heard of double/triple NAT-T without port forwarding ...

There is no specific need for port forwarding in any of the NATs when the traffic is originated outbound from the innermost client going out to a static globally routed IP. — Just like there's no need for it when making an HTTPS request from the same client system.

Do you mean VPN within UDP within VPN? You'll need intermediate VPN gateways for this.

No. L2TP and / or PPTP are notoriously flaky with NATs. But it's usually possible to get a single L2TP / PPTP VPN to function behind a NAT. This is because the NAT sees the L2TP or PPTP traffic and associates it with a single VPN client behind the NAT. If (when) there is a second VPN client of the same type, it breaks the association of which internal client the traffic goes to. Thus it usually breaks / prevents all such clients from working at the same time.



--
Grant. . . .
unix || die

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