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purecharger

macrumors newbie
Original poster
Feb 24, 2008
5
0
I have a Cisco VPN server at work that I'd like to connect to, but cannot get Mac OSX 10.6 (currently running 10.6.4, but it has never worked with 10.6) to properly route to hosts. The built-in vpn client connects without error, and shows a proper routing table, but none of the hosts are reachable.

Here is my routing table prior to connecting:

Code:
($:~)- netstat -nr
Routing tables

Internet:
Destination        Gateway            Flags        Refs      Use   Netif Expire
default            192.168.1.1        UGSc          131        0     en1
127                127.0.0.1          UCS             0        0     lo0
127.0.0.1          127.0.0.1          UH              2     1042     lo0
169.254            link#6             UCS             0        0     en1
192.168.1          link#6             UCS             3        0     en1
192.168.1.1        0:1c:10:27:c8:2d   UHLWI         133      501     en1   1198
192.168.1.134      127.0.0.1          UHS             0        0     lo0
192.168.1.255      ff:ff:ff:ff:ff:ff  UHLWbI          0        2     en1
192.168.4          link#8             UC              1        0  vmnet8
192.168.4.255      ff:ff:ff:ff:ff:ff  UHLWbI          0        2  vmnet8
192.168.110        link#7             UC              1        0  vmnet1
192.168.110.255    ff:ff:ff:ff:ff:ff  UHLWbI          0        2  vmnet1

Then after connecting to the VPN:

Code:
($:~)- netstat -nr
Routing tables

Internet:
Destination        Gateway            Flags        Refs      Use   Netif Expire
default            192.168.1.1        UGSc          138        0     en1
default            utun0              UCSI            0        0   utun0
10.10.3/24         10.10.220.152      UGSc            1        0   utun0
10.10.3.11/32      10.10.220.152      UGSc            0        0   utun0
10.10.3.175/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.193/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.195/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.201/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.202/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.203/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.204/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.205/32     10.10.220.152      UGSc            0       11   utun0
10.10.3.206/32     10.10.220.152      UGSc            0        0   utun0
10.10.3.208/32     10.10.220.152      UGSc            0        0   utun0
10.10.20/24        10.10.220.152      UGSc            0        0   utun0
10.10.21/24        10.10.220.152      UGSc            0        0   utun0
10.10.220/24       10.10.220.152      UGSc            0        0   utun0
10.10.220.152      10.10.220.152      UH             19        0   utun0
10.10.241/24       10.10.220.152      UGSc            0        0   utun0
10.10.242/24       10.10.220.152      UGSc            0        0   utun0
10.10.254/24       10.10.220.152      UGSc            0        0   utun0
127                127.0.0.1          UCS             0        0     lo0
127.0.0.1          127.0.0.1          UH              2     1042     lo0
169.254            link#6             UCS             0        0     en1
192.168.1          link#6             UCS             3        0     en1
192.168.1.1        0:1c:10:27:c8:2d   UHLWI         154      559     en1   1179
192.168.1.134      127.0.0.1          UHS             0        0     lo0
192.168.1.255      ff:ff:ff:ff:ff:ff  UHLWbI          0        8     en1
192.168.4          link#8             UC              1        0  vmnet8
192.168.4.255      ff:ff:ff:ff:ff:ff  UHLWbI          0        5  vmnet8
192.168.110        link#7             UC              1        0  vmnet1
192.168.110.255    ff:ff:ff:ff:ff:ff  UHLWbI          1        8  vmnet1
216.105.43.50      192.168.1.1        UGHS            0        0     en1

And the relevant part of ifconfig:

Code:
utun0: flags=8051<UP,POINTOPOINT,RUNNING,MULTICAST> mtu 1280
inet 10.10.220.152 --> 10.10.220.152 netmask 0xffffffff

My personal machine at work is 10.10.20.181, which is fully reachable when I connect through Windows:

Code:
($:~)- ssh ryan@10.10.20.181
ssh: connect to host 10.10.20.181 port 22: Operation timed out

Any ideas?
 
My apologies for bumping an old thread, but did you ever get this resolved Purecharger?

Running into this same exact problem on OS X Lion 10.7.2
 
My apologies for bumping an old thread, but did you ever get this resolved Purecharger?

Running into this same exact problem on OS X Lion 10.7.2

The actual problem? No - but in a roundabout way I did: I quit that job and work at a place that did their VPN config properly :)

Good luck!
 
How about increasing the priority of your VPN connection in System Preferences?
 
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