Setting up Watchguard SSL VPN on a Macintosh Computer

The beauty of being an IT technician, is that you have the possibility of learning something completely new every day. Along with this amazing opportunity, frustration can arise from trying to master a new skill or tackle a particular stubborn issue. Upon setting up a Watchguard SSL VPN on the Watchguard device itself and the client’s machines, I ran across a peculiar problem. A Macintosh computer on the network could not download the necessary SSL VPN client. The fix came from booting the computer into its 32 bit kernel, then allowing the installation to run its course. Since the SSL VPN client from Watchguard is a 32 bit application, the installer is forced to run in the 32 bit kernel. Here are the steps for getting the SSL VPN client to install on a mac if you are receiving the dreaded client.ovpn file is missing error.

1. Uninstall any current Watchguard SSL VPN software that is on the machine.

2. Make sure the Mac security options to allow software from “anywhere”(System Preferences->GateKeeper).

3. Reboot the MAC, but try and verify that the Mac is running in 32 bit mode.

4. If your Mac uses the 64-bit kernel by default, you can start up with the 32-bit kernel by holding the 3 and 2 keys during start-up.

5. Reinstall the SSL software.

6. Test the SSL VPN connection.


Thanks to Eugene at Watchguard for the fix.

August 04, 2014 by Lauren Winstead Category: General IT, Software 0 comments

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