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So here is a rough sketch of what my network currently looks like:

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From the .2 machine I would like to SSH into my .6 machine, however I am not even able to ping it. This all worked when I was on 1 network, so no silly configurations are missing for simple SSH, however having the extra router I now cannot access the .6 machine at all.

I was thinking of just opening an SSH port on the .254 router and accessing the machine that way (so I would SSH into my actual IP from the outside world), but I was wondering if this is the correct way to go about doing this. Anybody have any experience with a similar setup?

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Having a router with the same subnet on both sides of the router is usually not a good idea. You cannot make any easy distinction between the networks anymore (besides mac address) so it makes managing quite a bit more difficult.

Personally I would say, disable the router feature on the .254 router and just use it as a switch/bridge.

If that's not possible, than it would be good to change the subnet to something like 192.168.2.x and add a port forward so you can ssh to 192.168.1.254 to reach the .6 computer.

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Yeah, I thought it a bit odd that everything works even though they share the same subnet (I have them set to use different ranges of ips). The weird thing is I can't ping the .254 router from within the .1 router (and it does show up in the .1 router as being address .254). This makes me doubt attempting to SSH through it will work. –  KDiTraglia May 6 '13 at 12:39
    
It can work, as long as forwarding in both directions is enabled. But to save yourself from a large headache I would not recommend it. –  Wolph May 6 '13 at 13:12
    
Would this mean that the outside router would have 2 identities (I mean purely internally)? What my inside router thinks it's called, and what it think it's called based on it's own DHCP? Any idea why I can't ping the .254 router from inside my LAN? –  KDiTraglia May 6 '13 at 13:33
    
Hmm, for some reason I didn't think it would be as easy as just setting up subnets and suddenly everything would work. Finally sat down today and did so and everything suddenly worked. Thanks for the answer. –  KDiTraglia May 7 '13 at 21:51

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