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sorry to ask but i have asked misc before and they just kick my ass
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No need to be sorry at all! I totally understand
Ok judging by the information you provided it seems like some kind of routing issue....
Have you configured "Static" or "Dynamic" routing between the systems?
I personally recommend configuring OSPF between them!
Additionally are you using standard ipsec or GRE??
GRE is a better solution in my opinion however, is much more difficult to setup.
Have a look at the link I posted at the beginning of this thread as that will describe the methodology that I used.
I do also think that the psk <passphrase> should be put in "" another words:
In order to debug, I would first run a traceroute between machines and see where things are going wrong.
Additionally look at the routing tables of each system:
Cisco:
OBSD:
Start with that then let me know how you got on!