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Hi,

On 24-09-14 11:21, David Sommerseth wrote:
> On 24/09/14 10:26, David Sommerseth wrote:
>> On 24/09/14 10:15, Gert Doering wrote:
>>>> But to get to the point, that if I setup openvpn on my
>>>> droplet and let's say an evil admin sniffing my traffic for 3
>>>> months with tcpdump then decides to decrypt that traffic what
>>>> tools does he have (if any to do this). At this point he has
>>>> a pcap file and the openvpn server certificates and keys.
> 
>>> Now that is easy - OpenVPN does PFS, so the stored keys won't 
>>> help decrypt sniffed session traffic.
> 
>> If an attacker have sniffed the complete handshake and is in 
>> possession of the keys, I believe it is a theoretical
>> possibility to compromise the key exchange handshake.  Which
>> again gives you the access to the tunnel data.  If the attacker
>> in addition have access to client keys, then this process goes
>> even faster.  But it is correct that you don't get the raw key
>> out of the handshake.
> 
> Gert and I have had a private discussion regarding if it is
> possible or not to break the session key.  We both agree that it's
> not an easy task, and capturing data + having they key material
> alone isn't enough to break the session key.

I agree, OpenVPN does offer forward secrecy. At least when the setup
uses TLS-mode (like the howto of digitalocean the OP referred to).

Let me elaborate a bit. OpenVPN can run in two modes:
1. Static key mode (using '--secret <file>'). This uses a pre-shared
static key, which is not rotated at all. An attacker with that key and
a pcap can decrypt all traffic since the last time you (manually)
rotated the key. Unless you know what you're doing and have good
reasons to use it, do not use this mode.

2. Dynamic key mode. This uses TLS to set up a secure channel over
which the actual data encryption keys are exchanged. This mode
protects you as much as TLS does. By default, OpenVPN connections use
a dynamic key exchange, like (Ephemeral) Diffie-Hellman or - for older
versions - Ephemeral RSA. The TLS session keys will then exist at most
(1) between two session negotiations for ephemeral DH, (2) for an
OpenVPN connection for non-ephemeral DH or (3) for the OpenVPN process
lifetime for ephemeral RSA.

For a scenario like the OP describes (pcap + current memory dump), the
attacker can only decrypt traffic for which the current in-memory key
has been used (see above).

Note that this scenario restricts the attacker to be passive (i.e.
just traffic / memory dumps). An active attacker could use a
man-in-the-middle position to attack the cryptographic handshake or
implementation, like David describes. That however does not enable her
to 'go back in time' further then the validity of the keys used during
the attack. Traditionally, we recommend to use OpenVPN's tls-auth
feature as an extra layer of protection against man-in-the-middle
attacks. In this scenario however, the attack already has access to
the tls-auth keys, so that won't help you here. (Still, use tls-auth,
it protects you from a lot of other bad stuff.)

This ended up as more text than I intended. I hope it clarifies more
than it confuses ;)

- -Steffan
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