Hi all, I have an SBS2003 server behind Tomato (PPPoE DSL) with tcp port 1723 forwarded back for PPTP remote VPN users. I have the default NAT/GRE/PPTP helper enabled as well. I am able to do remote VPN into the SBS2003 server without any problems, but if I try and create an outgoing PPTP connection to Site X (on the server out to a backup XP box for backups) when a user from Site X has already established on incoming PPTP, the outgoing PPTP connection never works. However, if I create the outgoing PPTP from the server to SITE X and then have a user from SITE X connect incoming to the server, everything is fine. SBS2003==|Tomato|----Internet----|Site X with NAT router|====PCs (1xoffsite backup;1 x regular user VPNing into the SBS2003) I took our backup server and backup router and setup to my test lab to try and resolve the problem. I was only able to use DHCP for the WANs, and surprisingly the above problem went away! So basically the problem with PPTP passthrough was present when PPPoE WAN was used, and NOT present when DHCP for WAN was used. I'm wondering if the problem is with the NAT helper and/or iptables. Has anyone experienced this problem before? Any suggestions? I have tried both 1.21 and 1.23 firmware. Both exhibit the same problem. I did some searching on the forums and found a few people with PPTP issues in the past with older firmwares.