BlueCoat's ProxySG is one that runs tranparent SSL protocol detection
and breaks if openvpn traffic is coming in via 443. This proxy is able
to pass through other non-HTTP pure SSL traffic though and not just
HTTPS.

Vineet
On Fri, Mar 11, 2011 at 11:58 AM, Joe Patterson <j.m.patter...@gmail.com> wrote:
> 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-----
>>> Hash: SHA1
>>>
>>> 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-----
>>> Version: GnuPG v1.4.10 (GNU/Linux)
>>> Comment: Using GnuPG with Fedora - http://enigmail.mozdev.org/
>>>
>>> iEYEARECAAYFAk157MQACgkQDC186MBRfrqQdgCdGKarB9OcdlKSQaTxLXZIZnou
>>> qmoAn0G/9cfGHx6+NeWk2v0agOjRJCI9
>>> =SOiC
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>>>
>>
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