Take a look at a presentation that was done at Black Hat this summer.  
The presenters performed a MiM on a VPN connection.

http://802.11ninja.net/bh2002.ppt

The attack worked because of issues with the VPN implementation as 
Bernard points out.

On Wednesday, Oct 9, 2002, at 09:04 US/Eastern, Bernard Aboba wrote:

>> Thanks to all for the replies on this one, especially the outline 
>> below.
>>  A bit of additional info - I do use VPN's for connection security, 
>> so I'm
>> not really worried about MITM attacks via rogue AP's.
>
> Why not? Before relying on VPNs for wireless security, I'd advise you 
> to
> do a careful review of your IPsec/IKE implementation.
>
> A rogue AP can do a lot of damage to a VPN implementation -- like
> injecting disassociation and deauthenticate frames at will. In 
> addition,
> many IPsec implementations rely on group pre-shared keys (that's
> required by IKE Main Mode when the client has a dynamic IP address). 
> That
> means that there is effectively no IKE authentication between client 
> and
> server -- and some implementations don't even authenticate the VPN 
> server
> to the client after the IPsec SA is set up, they just use CHAP.
>
> Since a group secret isn't a secret at all, this allows any authorized
> user to set up a rogue VPN server. And if the installation does 
> something
> really foolish, like deriving the group pre-shared key from a 
> password, then the group
> pre-shared key can be cracked by an outsider, because IKE Main Mode is
> vulnerable to offline dictionary attack.
>
> Ironically, IKE Aggressive Mode does a better job in the dynamic client
> case, since you can have individual pre-shared keys for each client,
> although the identity exchange is exposed on the wire. However, many 
> VPN
> clients don't support Aggressive Mode, so you may be out of luck.
>
> The bottom line is that IPsec/IKE VPNs are no panacea when dealing with
> clients that have a dynamic IP address. Most of these issues don't 
> arise with
> point-to-point implementations, since in that case, both ends of the 
> VPN
> connection typically have a fixed IP address, and so IKE Main Mode 
> allows
> for individual pre-shared keys (and identity protection).
>
>
> --
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