Back in August 2007, I reviewed version 1.0.3 of Shimo, at the time an alternative to Cisco’s official Mac client for Cisco VPN (virtual private network) access. Shimo was a welcome solution that offered the benefits of Cisco’s own client (reliable connections, specialized connection settings) along with the ease of use of Mac OS X’s built-in VPN client (easier configuration, menu-bar access, no need to launch a separate application). However, version 1.0.3 of Shimo supported only Cisco VPN connections, and it still required you to install Cisco’s client.

Since then, Shimo has seen over a dozen minor updates as well as a major upgrade to version 2. In addition to bug fixes and improved compatibility, version 2 brings a number of big new features that make it an even better VPN-client alternative—and not just for Cisco VPNs (which are now supported without the need to install Cisco's client), but for other VPNs, as well: standard PPTP and L2TP; Racoon/IPSec; OpenVPN; AnyConnect; and Hamachi. You can now also use Shimo to connect to remote servers via SSH. (I was able to test Shimo with Cisco, PPTP, and SSH connections.)

For any type of connection, Shimo lets you save a profile that includes connection and authentication settings (including user, group, and certificate authentication methods), as well as actions (such as switching to a particular OS X network location or executing an AppleScript) to be performed whenever you connect. You can save as many VPN profiles as you need and quickly connect to any of them using Shimo’s menu-bar menu. (Note that you configure PPTP and L2TP connections in the Network pane of System Preferences, even though you can connect using Shimo.) If you’ve got multiple Macs and a Mobile Me account, Shimo can sync your VPN settings between Macs.

If you’re switching from other VPN-connection software, Shimo can import configuration profiles from Shimo, Cisco, vpnc, Racoon, and Open VPN; this feature is also useful for configuring multiple computers with the same settings or providing a standard configuration file for users across an organization. The developer even provides downloadable configuration files for specific VPN servers, and you can also import security certificates.

Like Shimo 1, Shimo 2 can automatically reconnect dropped VPN connections or when your network changes, and can automatically connect to a particular VPN whenever you switch to a particular network location or access a particular wireless network. (Although a useful improvement would be the capability to automatically connect to a particular VPN whenever you aren’t on a particular wireless network or using a particular network location; after all, you’re most likely to need a secure connection when on an unfamiliar network.) If your VPN terminates idle connections, Shimo can send packets over the network at a chosen interval to keep that connection alive.

Also like its predecessor, Shimo 2 lets you set a system-wide keyboard shortcut for connecting and disconnecting, and can notify you of a number of types of events, including connections, disconnections, and errors. For each event, you can choose to be notified by one or more methods: an audible alert, a dialog box, an AppleScript, a spoken message, or a Growl display. A useful statistics window displays information about your connection, including your secure IP address, connection time, and network traffic.

Shimo is also impressively flexible. For example, each profile can include multiple IP addresses and domain names for a particular VPN, and a number of advanced settings are provided to customize Shimo’s under-the-hood behavior.

One new feature that didn’t work for me is an option to “Automatically handle ‘Back to my Mac’ connections.” Many Back to my Mac users have found that the feature doesn’t work over VPNs, and Shimo claims to allow it to do so; in my testing, I was still unable to connect from one Mac to another using Back to my Mac when a VPN connection was active. However, to be fair to Shimo, I’ve had little luck getting Back to my Mac to work reliably at all, so it’s possible this feature may work better for other people.

Finally, another welcome improvement is that unlike the version of Shimo I covered back in 2007, Shimo 2 includes good documentation, including specific information about configuring Shimo for use with each supported VPN service (Cisco, Racoon, OpenVPN). However, I’d still like to see tooltips for each setting, given how confusing VPN settings can be for most users.

Whereas the original Shimo was a must-have for those forced to use Cisco’s VPN client for Mac OS X, Shimo 2 is worth considering for anyone who regularly connects to a VPN.