Windows 11 TAP won't come up.So routes and tunnel fail

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  • jngreene
    Junior Member
    • Oct 2024
    • 4

    Windows 11 TAP won't come up.So routes and tunnel fail

    Unless my decades of troubleshooting fail me.. The following error seems to be the root of the problem which results in the TUN/Tap device never reaching an up state, the wait timing out and failing route statements (cascading errors) and ultimately failure..

    OS/Software data
    Code:
    Server 2.5.9; Fedora 40
    Client 2.5.9 with OpenVpn GUI 11.31.0.0; Windows 11 Home 23H2
    Most pertinent Errors (Scrubbed full log available upon request).
    Code:
    Set TAP-Windows TUN subnet mode network/local/netmask = 10.69.0.0/10.69.0.1/10.69.0.2 [SUCCEEDED]
    Notified TAP-Windows driver to set a DHCP IP/netmask of 10.69.0.1/10.69.0.2 on interface {875FFDB8-8C40-40B3-96F7-9D602F148D2C} [DHCP-serv: 10.69.0.0, lease-time: 31536000]
    DHCP option string: 0f0e6772 65656e65 6d797374 2e636f6d 06080a00 0001d043 dcdc
    ​
    It appears that from somewhere it is getting the idea that with 10.69.0.1/10.69.0.2 is an IP netmask pair instead of a <gateway>/<ip> routing pair.

    Client.config is
    Code:
    client
    port 1194
    dev tun
    remote <server hostname>
    # TLS parms
    ca "<path_to_file>ca.crt"
    cert "<path_to_file>CaptainsReadyRoom.crt"
    key "<path_to_file>CaptainsReadyRoom.key"
    tls-auth "<path_to_file>ta.key" 1
    remote-cert-tls server
    tls-client
    pull
    verb 4​
    ccd/CaptainsReadyRoom file for the client on the server is:
    Code:
    ifconfig-push 10.69.0.1 10.69.0.2
    Uncommented lines of server.conf file is:
    Code:
    cd /etc/openvpn/
    local <server_inet_exposed_addess>
    port 1194
    proto udp
    dev tun
    ca <path_to_file>ca.crt
    cert <path_to_file>server.crt
    key <path_to_file>server.key
    dh <path_to_file>dh.pem
    topology subnet
    server 10.69.0.0 255.255.255.0
    ifconfig-pool-persist ipp.txt
    client-config-dir ccd
    route 10.69.0.0 255.255.255.252
    push "route <internal subnet1> 255.255.255.0"
    push "route <internal subnet2> 255.255.255.0"
    push "redirect-gateway def1 bypass-dhcp"
    push "dhcp-option DOMAIN greenemyst.com"
    push "dhcp-option DNS <internal DNS>"
    push "dhcp-option DNS 208.67.220.220"
    client-to-client
    keepalive 10 120
    tls-auth <path_to_file>ta.key 0
    data-ciphers AES-256-GCM
    max-clients 10
    user nobody
    group nobody
    persist-key
    persist-tun
    status openvpn-status.log
    log-append  openvpn.log
    verb 3
    explicit-exit-notify 1
    Suggestions please?
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