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I use several VPN clients, and have to switch among them many times throughout the day. Basically, I'm signing in and out of them all day, every day.

It's driving me nuts, so I'm planning on setting up a VM for each network that I need to be on, but that sounds ridiculous.

Is there a better way besides setting up a VM for each VPN client?

Is it even theoretically possible to have a VPN management tool that allows us to switch between VPN clients?

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What is the VPN client? Just Microsoft? – KCotreau Jun 28 '11 at 1:49
Personally, I regularly keep multiple VPN tunnels open all day long. You do not need to choose. – KCotreau Jun 28 '11 at 2:10
@KContreau: Multiple different VPN clients...Cisco, Forticlient, Checkpoint, Juniper. See this question for reasons not to use multiple VPNs and why it might fail:… – mlissner Jun 28 '11 at 17:56
Are these VPNs split tunnels or is all traffic sent over the VPN? If – ridogi Feb 28 '12 at 23:51
I think all traffic is sent, but I really can't be sure. Any way to tell? – mlissner Feb 29 '12 at 6:09

2 Answers 2

Setting up a VM for every client is going to be a gigantic drain of resources on your machine.

Sometimes, though, you may be connected to many VPNs simultaneously without any special effort. Let me explain.

VPNs perform two tasks:

  1. route all your traffic through a remote server;

  2. give you access to a remote LAN.

In doing task1, they change your default gateway, which (for Windows and Unix machines, but not for Linux) absolutely must be unique. Hence a conflict arises.

Thus the first requirement to have several VPNs running simultaneously is to keep your default gateway, the one you have before logging into any VPN; or in other words, not to allow any tunnel.

There may be a conflict with task 2 as well. VPNs give you access to remote LANs. For a simultaneous connection to work, it is necessary that all LANs correspond to distinct, non-overlapping subnets.

You can help in this by giving your home network an unusual range, something like But you cannot be sure that the remote LANs will cooperate. If they do, you are in business, because you will have a route to, say, another route to, one to, and so on.

Please keep in mind that the above applies both to the LANs, and to the IP addresses dished out to the tunnel, which are typically in the range 10.0.0x/24, and so on.

In other words, all private addresses ranges must be non-overlapping. If this occurs, and you have kept your own gateway, then you definitely can connect to many VPNs simultaneously, without the use of any VM.

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OS X natively supports L2TP over IPSec, PPTP, and Cisco IPSec. You can set up multiple VPN configurations and quickly connect as needed via the menu bar, or through the Network Preferences interface.

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