Do you have a pointer to a specific SSL proxy that you're talking about?

I have this sneaking suspicion that what you're actually referring to
is a transparent https proxy, which would most definitely *not* work,
as openvpn rides on top of ssl, but not on top of http on top of ssl.

A good test of this would be to try something like openssl
s_client/s_server on each side of the proxy, or netcat with ssl
support and make sure that if you try and pass non-http traffic
through it, that the proxy doesn't reject or otherwise molest it.

-Joe

On Fri, Mar 11, 2011 at 2:09 PM, Vineet Kumar <vineet.ku...@gmail.com> wrote:
> Thanks for your replies.
>
> So,
> - without --tls-auth
> - with tcp as the transport
> if we want to make openvpn purely SSL then are these the complete set
> of things to take care of?:
> 1. Move all P_CONTROL_* messages to be encapsulated in SSL
> 2. Stop adding reliability layer over SSL
>
> Let's say, theoretically, that the above 2 steps are taken care of
> (easier said than don, for sure). Will the resulting VPN setup then
> pass through transparent SSL proxies unbroken?
>
> Thanks,
>
> Vineet
> On Fri, Mar 11, 2011 at 1:35 AM, David Sommerseth
> <openvpn.l...@topphemmelig.net> wrote:
>> -----BEGIN PGP SIGNED MESSAGE-----
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>>
>> On 11/03/11 10:04, Gert Doering wrote:
>> | Hi,
>> |
>> | On Thu, Mar 10, 2011 at 05:04:48PM -0800, Vineet Kumar wrote:
>> |> Also, doesn't this make openvpn different from other SSL VPNs which
>> |> advertise the fact that they are truly SSL?
>> |
>> | Well, OpenVPN is "truly SSL", but it's not "using https as a browser would
>> | do to hide the fact that there is a VPN inside"...
>>
>> Kind of.  Gert is basically correct.  But it is important to understand that
>> OpenVPN doesn't use the SSL wire protocol directly, like the majority of SSL
>> applications does.  So all the SSL packets from OpenVPN are encapsulated in
>> a
>> kind of OpenVPN container.  Which is why some strict proxies or deep packet
>> inspection firewalls might not allow OpenVPN traffic.
>>
>> The reason for this is that OpenVPN is primarily written for the UDP
>> protocol.
>> ~ While SSL itself is very TCP oriented.  To my knowledge, there are no UDP
>> transport support in OpenSSL.  So OpenVPN uses OpenSSL differently,
>> intercepting the network connections and sending the data through OpenVPN's
>> own network socket infrastructure.  If OpenVPN's HMAC support (--tls-auth)
>> is
>> enabled, some extra bytes are added on top of the SSL packet itself.
>>
>> Of course, it would probably be possible (I have not investigated this) to
>> add
>> a feature which restricts OpenVPN to use the core SSL protocol, without
>>  this
>> encapsulation on top of the SSL packets.  However, when such a feature is
>> enabled, it would restrict the usage of TCP.  In addition, the --tls-auth
>> feature would not be useful in at all.
>>
>>
>> kind regards,
>>
>> David Sommerseth
>> -----BEGIN PGP SIGNATURE-----
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>> Comment: Using GnuPG with Fedora - http://enigmail.mozdev.org/
>>
>> iEYEARECAAYFAk157MQACgkQDC186MBRfrqQdgCdGKarB9OcdlKSQaTxLXZIZnou
>> qmoAn0G/9cfGHx6+NeWk2v0agOjRJCI9
>> =SOiC
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>
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