OpenVPN + OS X Leopard + Shimo Problems

  • I've been reading the posts, and trying to figure out where my issue lies, but its time to turn to you guys :-)

    I have a Pfsense running at home and decided to move from having port 22 open from my office, to just having a VPN I can use anywhere…  I followed the tutorials listed here and progressed onto connectiong w/o any issues.

    I am running OS X 10.5.7 on a MBP and using Shimo ( to connect.  I've been using Shimo for years to connect to my Cisco Concentrator at the data center and noticed it supports a lot more VPNs, IPSec, OVPN, etc.

    I can connect successfully, but cannot connect/ping/ssh/ftp/http to anything, zero connection :-(

    Here is my configuration:

    LAN = (

    OpenVPN Server Config:

    Protocol: UDP
    Dynamic IP: Checked
    Local Port: 1194
    Address Pool:
    Local Network:
    Crypto: BF-CBC (128-bit) (DEFAULT)
    Authentication Method: PKI

    All the correct keys are pasted in.

    Firewall Rules:


    Protocol *
    Source Port *
    Destination: (Tried both LAN net & *)
    Gateway *


    Protocol UDP
    Source *
    Source Port *
    Destination *
    Destination Port 1194 (OpenVPN)
    Gateway *

    Shimo is configured with OpenVPN, and TUN, Certs/Keys & IP. And reconnect of 30 seconds.
    I receive no errors on the Mac and actually see myself connected on the PFSense:

    Jun 12 10:39:31 openvpn[35940]: [client-macbookpro-windows] Peer Connection Initiated with
    Jun 12 10:40:32 openvpn[35940]: Re-using SSL/TLS context
    Jun 12 10:40:34 openvpn[35940]: WARNING: 'link-mtu' is used inconsistently, local='link-mtu 1541', remote='link-mtu 1542'
    Jun 12 10:40:34 openvpn[35940]: WARNING: 'comp-lzo' is present in remote config but missing in local config, remote='comp-lzo'
    Jun 12 10:40:35 openvpn[35940]: [client-macbookpro-windows] Peer Connection Initiated with

    And here's the output of a netstat on my MBP:

    Destination        Gateway            Flags    Refs      Use  Netif Expire
    default            66.174.XXX.XXX      UGSc      94      11  ppp0
    66.174.XXX.XXX      75.251.XXX.XXX    UH        95        3  ppp0
    75                ppp0              USc        5        0  ppp0
    127                UCS        0        0    lo0          UH          6    1628    lo0
    192.168.10      UGSc        1      785  tun0      UGSc        0        0  tun0      UH          3        0  tun0

    Destination                            Gateway                        Flags      Netif Expire
    ::1                                    link#1                          UHL        lo0
    fe80::%lo0/64                          fe80::1%lo0                    Uc          lo0
    fe80::1%lo0                            link#1                          UHL        lo0
    ff01::/32                              ::1                            U          lo0
    ff02::/32                              ::1                            UC          lo0

    I think I've provided about all the info I can, any help on this would be GREATLY appreciated.



  • Check your LZO compression setting, your logs are complaining that LZO compression is enabled only on one side of your tunnel.

    Same with MTU, mismatched settings.  Not familiar with Shimo so check your settings there match your pfSense OVPN settings

  • You're the man! I had (in Shimo) Compression set to Disabled, and changed it to "Never" and somehow that fixed it…. go figure :-)


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