Is the PPTP server enabled on the 'other' pfSense firewall where the clients 
are connecting *FROM*? That may be your problem... see here:  
http://www.pfsense.org/index.php?option=com_content&task=view&id=40&Itemid=43
'
Specifically this text:

Limitations
    * Because of limitations in pf NAT, when the PPTP Server is enabled, PPTP 
clients cannot use the same public IP for outbound PPTP connections. This means 
if you have only one public IP, and use the PPTP Server, PPTP clients inside 
your network will not work. The work around is to use a second public IP with 
Advanced Outbound NAT for your internal clients. See also the PPTP limitation 
under NAT on this page. 

Tim Nelson
Systems/Network Support
Rockbochs Inc.
(218)727-4332 x105

----- "Christopher Iarocci" <[email protected]> wrote:

> Tried putting an unused LAN IP in the server field, no difference
> whatsoever.  It gives me the same exact errors on the client side and
> in the
> PFSense logs.  Anything else I can try?  Just as an FYI, the clients I
> am
> testing with are XP Pro and Vista Ultimate.  Both are behind another
> PFSense
> firewall.  I only try a single machine at any one time.  I can't get
> my head
> wrapped around the fact that it used to work like a charm with the
> same
> exact config.  I even went back into previously saved configs and
> compared
> them and there is no difference.  It worked with this config as
> recently as
> 12/29/07 (last PPTP log entry).
> 
> Christopher Iarocci
> Network Solutions Manager
> Twin Forks Office Products
> 631-727-3354
> 
> -----Original Message-----
> From: Chris Buechler [mailto:[email protected]] 
> Sent: Friday, January 09, 2009 2:31 PM
> To: [email protected]
> Subject: Re: [pfSense Support] Multi-WAN PPTP?
> 
> On Fri, Jan 9, 2009 at 1:08 PM, Christopher Iarocci
> <[email protected]>
> wrote:
> > Chris,
> >
> > Does it matter which IP address on my LAN it is?  Should it be the
> LAN IP
> of
> > the PFSense box, or something other than that?
> >
> 
> Just pick an unused IP on your LAN.
> 
> 
> > Does the radius server see requests coming from the IP address
> specified
> > there or the LAN IP?  In the past with the WAN IP in that field,
> requests
> to
> > the radius server came from the LAN IP.
> >
> 
> The IP of the interface closest to the RADIUS server, usually LAN.
> The
> server IP is just for PPTP client - server communication.
> 
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