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Thread: VPN Issues

  1. #1


    Member Since
    Mar 31, 2011
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    VPN Issues
    Brand new Mac user, sorry for the noob question.

    I've set up my PPTP VPN which goes to a Watchguard Firewall, but I am unable to resolve any machines on the remote (Windows) domain by hostname when connected. I can ping by IP, but not just the hostname.

    What am I missing? When the VPN is connected I see that it's pulling the correct DNS servers. I did read one tip to add "local" into the list of search domains under the VPN settings, but no luck. Any help?

  2. #2

    louishen's Avatar
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    What is your ip address and the IP format of the windows network

    eg, if your router uses 192.168.0.XXX and the remote network uses 192.168.0.XXX, then VPN will not work since it will look up any ip connections on your local network

    Either your home network or the work network needs another private adress psace, eg, at home I have 192.168.0.XXX, while work has 192.168.99.XXX

    If work will not change their adresses then your home network needs to be changed to 192.168.XX.XXX
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  3. #3


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    Different IP schema. I'm at home with 192.168.1.x, I'm going to a 10.0.0.x network.

  4. #4

    louishen's Avatar
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    what happens when you select Connect to server from the finders Go menu and enter a remote IP address from there
    Member of the Month September 2008 & August 2012 | Found advice useful? use the rep system

  5. #5


    Member Since
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    Using IP addresses are fine over the VPN, I can RDP and connect to server shares. It's using the hostname that I'm having problems with. Seems like a DNS issue, but when the VPN is connected, I see that I'm pulling the correct DNS server.

  6. #6

    MacsWork's Avatar
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    Macs don't resolve NETBIOS like Windows.

    When browsing you need the FQDN of the machine you are connecting to. Bonjour browsing will only occur on the LAN and not traverse the VPN. Therefore the machines that show up in the Shared section of the sidebar in the Finder are only local LAN computers.

    Try myserver.mydomain.local (eg: server01.contoso.local) across the VPN. That should work. Whatever your domain extension may be .local, .private, .com etc.

    Problems????
    Also be sure that the VPN settings are sending all traffic across the VPN, and that the VPN is on top of the list of interfaces in System Preferences.

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