Vincent Danen introduces Shimo, a first-class VPN connection application for OS X that works with OpenVPN, Cisco’s VPN, IPSec, PPTP/L2TP, SSH, and more.

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Mac OS X 10.6 provides better VPN connectivity than previous versions did; however, if you want something feature-rich and reliable, consider giving Shimo a try. Shimo is a first-class VPN connection application for OS X that works great with OpenVPN, Cisco’s VPN, IPSec, PPTP/L2TP, SSH, and more.

In OS X 10.5, if you wanted to connect to a Cisco VPN service, you had to find something other than the built-in OS X VPN client. Shimo worked admirably with 10.5 and even though 10.6 provides much better Cisco VPN client support, Shimo still beats it.

To begin, download and install Shimo, then start it up. Click on the door icon in the menu bar and select Preferences. Here is where you define Shimo’s operating configuration and the various connection profiles. Head over to the Profiles tab and use the “+” icon to select a VPN connection type to create. To create a Cisco VPN connection, use the “vpnc (Cisco Alternative)” profile.

In the General tab, give the profile a unique name; this will show up in the menu pulldown for connections to initiate. In the Authentication tab, you define your username and (optionally) a password, as well as the authentication method. Under the Connection tab, enter in the IP or hostname of the Cisco VPN server to connect to. Here you can also enable automatic reconnection in the event that the VPN connection drops. There are also other options you can set here as well to further tweak the VPN connection.

Once that is done, you can use the menu pulldown to connect to your VPN. To further tweak Shimo, go back to the Preferences and under the Advanced tab, enable the sending of keep-alive packets in order to keep the VPN up during inactivity. You can also enable an automatic reconnection on network changes (such as moving from one wireless network to another).

In the Network tab you can tell Shimo to automatically initiate connections based on network locations. For instance, you can have it initiate a connection to a particular profile if you start using a particular wireless network, or take advantage of network location services in System Preferences to do the same based on defined network locations. And if you use MobileMe, you can have Shimo synchronize profiles to other computers on the same MobileMe account.

Shimo offers a number of features above and beyond what OS X provides out-of-the-box that make it useful and compelling. Throw in Growl notifications, a statistics window that shows you how long you have been connected, as well as network transmission statistics, and you find an app with plenty of goodies useful for anyone that requires the use of a quality VPN client application.