Ping only works after Remote Desktop connection is made

Discussion in 'Windows Networking' started by g18c, Nov 14, 2007.

  1. g18c

    g18c Guest

    Hi, i have a bit of a strange problem and i cant work out why.

    I have a remote XP PC: OpenVPN connection
    with route added for to go via the VPN

    Now on the other end the network consists of:

    I have a OpenVPN server inside the lan on
    Its default gateway is

    I have 3 Windows Servers,, 247 and 248. All gateways are
    set to

    I have a ethernet router on the network,, it has a route
    added for to go via, and route added for to go via also).

    The trouble is, i can remotely connect and ping to the OpenVPN router
    fine and also the ethernet router, however when i ping any of the
    Windows boxes it times out. But i can open up Remote Desktop and
    connect to the windows box without problem, infact if i am running
    'ping -t' it will suddenly come alive but only after the
    RDP connection is made.

    Is this something funny with the routing? I want to keep the OpenVPN
    server internal to the network and i appreciate it is hitting the
    ethernet router then being passed to the OpenVPN but something is
    weird as it fires up RDP fine but not ping. No firewalls are enabled
    on any of the boxes. If i log into ssh on the OpenVPN router or
    ethernet router i can ping from that to the windows boxes fine.

    Its as if a ICMP redirect is issued, and all is well after the 1st
    connection. Not too sure but could anyone be kind enough to enlighten

    Many thanks in advance,

    g18c, Nov 14, 2007
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  2. g18c

    g18c Guest

    Actually i think this may be an issue with the firewall, as the ping
    request has entered the network via the OpenVPN server, it hits the
    windows box. The windows box replies, but will go via the default
    gateway, the default gateway sees the ping reply but as it has not
    seen any ping request it drops the packet. I dont understand however
    why the ping would work after the RDP connection is made, unless an
    ICMP redirect has told the windows box not to bother using the default
    gateway but instead to reply via the OpenVPN server? Sorry if this is
    getting off windows topic, i thought it was the windows boxes
    initially but not so sure now.


    g18c, Nov 14, 2007
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