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I would like to connect Mac OS X (Lion) with Windows Server 2008 (R2) using IPSec natively. Simplest possible settings: No certificates, no tools, no specials. Just a Windows Server with IPSec "Pre-Shared Key" Authentication. Looks like an easy job, but after weeks of research I still have no success.

Attached there's a screenshot of the Windows settings. It works perfect with Windows clients, it doesn't matter which version. The whole rule is based on a 1to1-connection, that means the client is connecting (behind a NAT) to the Server (internet-facing). There are no server hardware/network-firewalls, it's just plain simple:

CLIENT -> NAT-Router -> "The Internet" -> Windows Server

But whatever I tried in OSX (Leopard, Snow Leopard, Lion) - no succes. Tried tools like IPSecuritas - no success.

I could provide details about the IPSec error logs (handshake-issues) but first I thought I just ask - I can't imagine I am the only in the world connecting OSX->Windows with plain simple IPSec...

Thanks, Ceka

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I've setup a L2TP/IPSec server on 2008R2, and we have numerous OSX (and other OS) clients connecting to it. What kind of errors are you getting, and are other clients able to connect to that IPSec server without any issues?

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