[iodine-users] Iodine on OSX - Created tunnel, unable to SSH over it?

[Victor Hooi]

Hi,

I am attempting to use Iodine 0.6.0 to tunnel. from OSX to a Linux server,
then SSH over that tunnel to the server.

The server is Ubuntu, running on an Amazon EC2 instance.

The client is OSX 10.8, running Iodine compiled via Homebrew.

On the server side, I have:

> sudo iodined -c -fP test 10.0.0.1 <tunnel_domain>
> [sudo] password for victorhooi:
> Opened dns0
> Setting IP of dns0 to 10.0.0.1
> Setting MTU of dns0 to 1130
> Opened UDP socket
> Listening to dns for domain <tunnel_domain>


I had to add the -c flag, otherwise I got messages like:

.3 not ok.. got BADIP (Try iodined -c)..
> .got BADIP (Try iodined -c)..


(Still not quite sure about the mechanics behind this).

On the client side, I have:

Victors-MacBook-Pro:~ victorhooi$ sudo /usr/local/sbin/iodine -fP test
> <server_ip> <tunnel_domain>
> Password:
> Opened /dev/tun0
> Opened UDP socket
> Sending DNS queries for <tunnel_domain> to <server_ip>
> Autodetecting DNS query type (use -T to override)......
> Using DNS type NULL queries
> Version ok, both using protocol v 0x00000502. You are user #0
> Setting IP of tun0 to 10.0.0.2
> Adding route 10.0.0.2/27 to 10.0.0.2
> route: writing to routing socket: Can't assign requested address
> add net 10.0.0.2: gateway 10.0.0.2: Can't assign requested address
> Setting MTU of tun0 to 1130
> Server tunnel IP is 10.0.0.1
> Testing raw UDP data to the server (skip with -r)
> Server is at 10.220.167.82, trying raw login: ....failed
> Using EDNS0 extension
> Switching upstream to codec Base128
> Server switched upstream to codec Base128
> No alternative downstream codec available, using default (Raw)
> Switching to lazy mode for low-latency
> Retrying lazy mode switch...
> Server switched to lazy mode
> Autoprobing max downstream fragment size... (skip with -m fragsize)
> 768 ok.. 1152 ok.. ...1344 not ok.. ...1248 not ok.. ...1200 not ok..
> ...1176 not ok.. ...1164 not ok.. will use 1152-2=1150
> Setting downstream fragment size to max 1150...
> Retrying set fragsize...
> Connection setup complete, transmitting data.
> iodine: Hmm, getting some out-of-sequence DNS replies. Setting interval to
> 1 (use -I1 next time on this network). If data traffic still has large
> hiccups, try if -L0 works better.


I am able to ping 10.0.0.2, but not 10.0.0.1 (Request timeout). Also,
attempting to SSH to 10.0.0.1 seems to just time out as well. The Amazon
server is running SSH on standard port 22, using key-based authentication.

I'm not sure of the significance of the "Can't assign requested address" on
the client side.

SSH-ing to 10.0.0.2 fails with connection refused - I assume because my OSX
doesn't have a SSH server running.

Are there any steps I need to get the SSH working over the tunnel?

Let me know if I can provide any further information that might help.

Cheers,
Victor
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