At the office I just replaced an old Sonicwall with a pfSense box. Everything has been working great but I'm having issues with the PPTP server. Here is the situation:

Office psSense 1.2.2 then upgraded to 1.2.3-Feb19 (issue is present on both cases) Office WAN: xxx.xxx.xxx.26/29 (xxx.xxx.xxx.27, xxx.xxx.xxx.28, xxx.xxx.xxx.29 and xxx.xxx.xxx.30 assigned to WAN with CARP VIPs and used in 1:1 NAT by several servers)
Office LAN: 192.168.0.0/24
Office DMZ: 192.168.2.0/24
Office PPTP server: 192.168.0.253 with client range 192.168.0.224/28

At home I'm also using a pfSense box:

Home pfSense 1.22
Home WAN: Assigned by cable ISP with DHCP
Home LAN: 192.168.1.0/24
Everything allowed outbound from LAN

When I try to connect to the PPTP server at the office from home I get a 619 error after it gets stuck at "Verifying User name and Password" (in Windows XP). However I have no problems connecting (from the same XP PC) to the Monowall PPTP server at our colocation. If I connect the cable modem directly to my PC then I can connect to the PPTP server at the office no problem.

I tried all the combination of "Clear DF bit instead of dropping" on or off on both pfSense boxes with no success. Another odd thing is that if I PPTP to the colocation (using it as a gateway) and the try to PPTP to the office, it works!

Everything works as long as only 1 pfSesne is involved with the connection. From similar cases I found searching this board and comparing the logs, it looks like the GRE packets are not flowing between the two pfSense boxes.

I ran out of ideas, so any help and suggestion is welcome.
I posted the pfSense logs on this post on the forums:
http://forum.pfsense.org/index.php/topic,14456.msg76525.html#msg76525

Max

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