I’ve been having trouble with a Windows 7 client connecting to a PPTP VPN endpoint on Mac OS X 10.6 (Snow Leopard) Server. The client authenticates just fine, and can access resources on the LAN, but connections time out when connecting to remote servers.
The simple solution was to configure the VPN client to only tunnel LAN traffic through the VPN, but that undermined one or our reasons for having a VPN: Securing connections from public WiFi hotspots.
For a long time, I assumed the problem had something to do with the routing, but after an hour or two with a packet sniffer hooked to the server, I discovered that TCP sockets to the problematic servers were being established, and, often, significant amounts of traffic were being passed back and forth. I also noticed that the conversations were interspersed with packet fragmentation errors.
Ah Hah! Something must be screwy with negotiation of the MTU. With a little digging, I found some instructions for adjusting the MTU, which I’ll summarize here: