Bryan,

Setting everything up like you have documented, great directions btw, did not 
change my end result.  If I disable NAT-T, I am prompted for a password every 
time and it does connect but fails to route anywhere.  If I enable NAT-T, it 
works as advertised IF I somehow get prompted for a password.  I never know 
when I will get a prompt for a password.  I can’t find a relationship or reason 
as to why it works or not even when I did not make any changes for several days.

I am now investigating the certificate part of your documentation to see if 
that makes any difference on the Mac OS X side.  Not really planning to do VPN 
on the phone, yet.  Thanks for your help.

If that doesn’t work, I guess the next step would be to try a software openvpn 
client.

Paul Galati
paulgal...@gmail.com



On Aug 20, 2014, at 1:59 PM, Bryan D. <pfse...@derman.com> wrote:

> I've not used the OS X client, but (just having had a quick look at it), it 
> appears to be similar to the iOS client (same code base?).  As such, some of 
> the information on a large posting I did about setting up IPSec VPN may help 
> (http://www.derman.com/blogs/Setting-Up-iOS-OnDemand-VPN).
> 
> Specifically, there's some info on preventing the Xauth password from being 
> prompted for during each connection -- see in section 2.b) Connection 
> behavior on http://www.derman.com/blogs/iOS-IPSec-VPN-OnDemand-Setup.
> 
> It's quite possible that using the indicated strategies (i.e., using the 
> Apple Configurator and manually editing the profile XML) would also work with 
> OS X.  If you try it and it does, please post a comment on the site (and 
> elsewhere?) so others can also benefit.

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