[stunnel-users] Safest suggested client/server stunnel configurations to prevent MITM attacks

[Leandro Avila]

>________________________________
> From: Michael K. Avanessian <michael at mka.net>
>To: "stunnel-users at stunnel.org" <stunnel-users at stunnel.org> 
>Sent: Friday, October 19, 2012 10:41 PM
>Subject: [stunnel-users] Safest suggested client/server stunnel configurations to prevent MITM attacks

>I’m currently tunneling SSH over SSL using stunnel.
>I thought that stunneled ssh data was safe.  However, recently I’ve read that if going through a sophisticated http/https proxy, it’s possible to be hacked by a “legitimate” mitm attack to fool an SSL client.

Tunneled and not-tunneled SSH data _is_ safe. The SSH protocol is pretty secure by itself. 

My understanding is that to pull off the type of SSL/TLS data inspection that you mention
http://www.sourcefire.com/security-technologies/network-security/ssl-encryption-decryption

there has to be some work done on the client side of the connection. (Install a custom

CA certificate in the trusted certificate store of the client machine)

So even if you were on such a network, as long as your "attacker" does not have control
of your machine. the SSL/TLS protocol will protect you because of the way keys (certificates)
are verified. (Notice the key word here is verified)

> 
>Is it still possible to configure stunnel so that ssl can’t be compromised between both ends?
> 
>I’m going to take a wild guess here; which I’m sure I’m probably wrong.  But, could I just install stunnel; and, let it create automatically a self-signed (stunnel.pem) certificate file… then just copy that file to the stunnel install on the other end?  That way both sides are already aware of each other’s public keys; and, wouldn’t be vulnerable during the initial unencrypted handshake?
> 
>I’m sure I’m probably way off; and, there’s more I need to do in stunnel’s configuration to further ensure the SSL won’t be compromised.. such as the stunnel “verify” setting.  I’m not sure which setting to have it; and, what it actually does.
> 
>I’m hoping someone could shed some light on this with simple suggested clientà server configs that would keep ssl uncompromised as much as possible.
> 
>Thanks in advance!

The configuration you are looking for stunnel involves the verify level 3 setting on the config
(Verify peer with locally installed certificate)

Plus the key management involved to set that up.

Take a look a this document. It is a little out of date. BUT the part about setting up the
certificates on client and server still applies. and is a good way to start
http://www.symantec.com/connect/articles/remote-desktop-management-solution-microsoft

Hope this helps



Leandro Avila
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