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Old 04-25-2012, 03:18 PM   #1
Join Date: Oct 2011
Posts: 5
Cisco VPN - DNS Issues

I've put this off for way too long, and it's really starting to bug me.

I seem to have an issue with the my work VPN. We use the Cisco VPN connection and I've successfully set up a Cisco VPN connection. The problem is, when I connect to the VPN, it appears that it only uses my local DNS server for lookups. For instance, if we had a handful of servers at my remote workplace, and I can't get to them, no matter what, by name, but I can get to them via IP (confirms DNS issue).

When I do a DNS lookup via dig from my osx system, I query it by way of:

dig servername01

It times out (obviously).

When I query from a known internal name server like so:

dig @ servername01

It returns immediately the server name and IP.

So, I know that the name server is working, so now I blame my OSX system for not handling this correctly.

Now, here's the weird thing - my VPN connection automatically gets assigned two DNS ip addresses, and the primary IP of it is the one from above, which works when I query the DNS system) and my wifi connection still uses my local DNS ( So, I have internet and I would assume that, if it cannot find something in the 10.x.x.x subnet, it would try the VPN DNS servers. This is not what it does though

So, what I then tried was setting the "Service Order..." in network preferences, and put the Cisco VPN at the top and my wifi one below that one. I even restarted the VPN connection, and still it does not use the remote workplace DNS settings.

The workaround I keep having to do is go into my wifi DNS settings and manually assign the remote DNS servers (primary is set as the one from above - After I hit apply, I can ping and access servers via name.

The additional problem with this is, now my internet goes through my workplace, so when I disconnect from the VPN, I now have to go back and remote the workplace DNS from my wifi adapter to use the default local DNS ( server - it gets very annoying after doing it for this long.

I know when I used to use Microsoft Windows - I'd connect to the VPN and them make sure "Use default gateway on remote network" was unchecked, and that would allow my to use the internet via my local DNS and everything else (such as accessing remote machines in the workplace) would go through my work DNS.

I've confirmed that this works fine in Windows and Linux (Ubuntu) by default, but in OSX it seems like the "Service Order..." doesn't really do what it's suppose to and it appears that the routing doesn't work the way I would expect.

Anyone have any ideas?

PS - This has been an issue since Snow Leopard and I'm currently running Lion.
drewrockshard is offline   Reply With Quote
Old 07-03-2012, 08:45 AM   #2
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Join Date: Jul 2012
Posts: 1
New Location

I created a new location in Network Prefs.
In there I put the remote DNS and the local DNS.
And specified the search domain for the remote site.
For me this works on line and off line.
But I am not using Cisco.............
jamiebs is offline   Reply With Quote

cisco, dns, networking, vpn

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