VPN S2S (IPsec) Azure - the server itself cant reach Azure Virtual Network

  • Hi,

    I did setup a VPN conection S2S with an Azure Virtual network.
    Everything works fine, but with one exception.

    I cant reach noting as destination Azure virtual network and source pfsense server itself.

    To make my self more clear.

    I have an AD (active directory) forest setup on Azure Virtual network.  I can reach the AD master from my LAN:

    Here is a ping from my workstation, behind pfsense

    –- admsweasvm01.eu.buddyguard.tech ping statistics ---
    4 packets transmitted, 4 received, 0% packet loss, time 3003ms

    When I am pinging from pfsense router I cant reach admsweasvm01.

    The reason I want to reach the Azure AD server from pfsense router is to setup the LDAP.
    As port 389 I can reach it from my workstation, behind pfsense :

    telnet admsweasvm01 389
    Connected to admsweasvm01.
    Escape character is '^]'.
    ^CConnection closed by foreign host.

    But from pfsense router I cant.

    All the tests shows there is no issue with the VPN or firewall on the destination, since everything working from my station so that means is an issue with pfsense and I have no clue where to start to dig in.

    Any ideas?

    Thank you!

  • Found the issue that I could not ping.
    The  traffic from pfsense is not going via lan interface automatically. If I am specifying the interface I have trafic:

    PING ( from 56 data bytes
    64 bytes from icmp_seq=0 ttl=127 time=39.681 ms
    64 bytes from icmp_seq=1 ttl=127 time=39.773 ms
    64 bytes from icmp_seq=2 ttl=127 time=39.590 ms

    –- ping statistics ---
    3 packets transmitted, 3 packets received, 0.0% packet loss
    round-trip min/avg/max/stddev = 39.590/39.681/39.773/0.075 ms

    Now I wonder I I tell to LDAP to bind to specific interface ?

  • I did figure it out.

    I have created a "LANGATWAY" that is my pfsense LAN interface IP adress ( then i have created a static route Azure virtual network via "LANGATEWAY"


    Name Interface Gateway Monitor IP Description Actions
    LANGATEWAY LANIPV4 Lan gateway

    Static Routes LANGATEWAY - LANIPV4

    Hope this will help others that will face same issue.

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