Mac - Windows VPN problem

Feb 23, 2007
Reaction score
This problem has been dragging on for a while now and I'm going round in circles.

A (mainly) Windows network that I manage needs to be accessed by a MacBook (OSX 10.4) user over VPN.

The network is protected by an IPCop firewall on which a certificate authorised VPN has been set up; this part is OK. The network is 192.168.1.x /24.

On the MacBook I've set up IPSecuritas to connect via VPN to the network; this bit is also OK in that IPSec starts and runs OK, the firewall log on the network shows the VPN as open and an incoming connection from the MacBook. Network address of the Mac is

The Mac needs to access email and word documents; the email server is a POP3/SMTP server at and the documents are all on a PC at on a peer-peer network with the appropriate folders shared.

The Mac can connect to email fine, send (SMTP) and receive (POP3) are both OK over VPN.

The Mac can ping every machine on the network over the VPN.

BUT, no way can I get the Mac to see the document server over the VPN. It's fine when it's physically on the network but over the VPN, nothing, zilch.

When the Mac is physically on the office network it sees all the shared Windows machines perfectly OK and, as I said, over the VPN it can ping them. I've tried everything I can think of; using GoTo Server on Finder to go to the IP address merely results in a message that the server cannot be found on the network. If I browse to the document server IP address with Safari then it can sort of "see" it if I force it to port 139 but does nothing. A port scan over the VPN shows ports 135, 139, 445 and 1793 open on the "server".

The Firewall log shows attempted connections to the server but no useful error messaging.

Does anyone have any ideas as to what I could possibly try next? I really have to get this working and the client is getting a little peeved over the delay!! :)

I'd really appreciate any sensible suggestions.



Shop Amazon

Shop for your Apple, Mac, iPhone and other computer products on Amazon.
We are a participant in the Amazon Services LLC Associates Program, an affiliate program designed to provide a means for us to earn fees by linking to Amazon and affiliated sites.