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I have the following home network:

Ubuntu 12.04.4 -> Router 1 -> Router 2 -> Ubuntu 12.04.2

I am able to make SSH connections if the machines are in one local area network as follows:

Ubuntu 12.04.4 -> Router 1 -> Ubuntu 12.04.2

but I have issues to instantiate SSH session between 12.04.4 and 12.04.2 machines(in the first case).

I guess the issue is that they have the following IP addresses assigned:

12.04.4   -  192.168.0.4
12.04.2   -  192.168.1.100

and because of this they are not in the same network.

Could anyone tell if I can instantiate SSH session in this case?

Note, I can reset routes to factory settings any time and configure them as I like.

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    No time for full answer, but take a look for port forwarding options in router 2. You want to forward port 22 to 12.04.02 port 22. – Olli Feb 22 '14 at 23:52
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You're using private IP adresses on your LANs (192.168.0.0/16), which is perfectly normal, but these are also known as "non-routable" IP addresses.

It means that Internet routers automatically drop packets that are bound to such IPs, but I don't know the behavior of consumer routers (I assume it's what you're using here).

You should first check that you can at least reach for the machine you're trying to log into through SSH :

"traceroute -n IP2" or "tracepath -n IP2" from a command shell on host with IP1

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