MacOS – way to connect to office VPN using parallels (windows) but surf on host Mac OS X

Once you've checked the "Open your Windows files and web links using Mac applications", the following should work (providing the file resides in one of the folders shared from the Mac according to this VMware Fusion guide):

• Right-click on one of the file types you wish you open in the VM and click "Open" or "Open With..." if the program already has an associated application (if you selected "Open", in the window that appears, check the "Select the program from a list of installed programs" radio button and click OK).

• In the window that appears there should be a VMware icon in the top-left that says "Default Host Application", select it and click OK. (You can also check the "Always use the selected program to open this kind of file" so that it opens with the host application next time too).

• If the VMware icon is not in the top-left, you may have to drop down the list with the "Other Programs" heading and you should see it there instead.

  

The document in the VM should now open in the default application on the host. For example, a pdf should open with Preview and a docx with Word for Mac.

It seems odd that your machine is attempting to use aggressive-mode in phase 1 of the IPSec connection. From what I can see, the default in 10.8.5 is to use main-mode. I'm wondering if you've modified the file at /etc/racoon/racoon.conf in trying to get this working? Can you post the contents of the file at /etc/racoon/racoon.conf?

Alternately, it may be possible to duplicate the configuration file that the L2TP/IPSec connection in System Preferences is using, and modify it slightly (configure to use main-mode) to see if that helps. Unfortunately, that configuration file is created at connect time, and is copied into /var/run/racoon/fqdn.of.host.conf. This file is also readable only by root (to protect the PSK that's stored inside of it). If you're quick, you can prepare a Terminal command that will copy that config file, initiate the VPN connection from System Preferences or the menu bar, and perform the copy command while the VPN is attempting to connect (you may have 5-10 seconds to perform the copy). Here's the command that you'd run right after initiating the VPN connection:

sudo cp -Rp /var/run/racoon/vpn.aec.com.br ~/Desktop

That file has permissions that disallow users from reading it. Use the command to make it readable:

sudo chmod 777 ~/Desktop/vpn.aec.com.br

NOTE: the file that you've copied onto the Desktop contains your PSK. You should not post this file (unmodified) to this website. If you would like to post this configuration file for troubleshooting, obfuscate the value of shared_secret before posting.

You can configure the VPN connection to use main-mode by modifying the configuration file that you've copied onto your Desktop. Open that file in any text editor, and locate the line that says exchange_mode. You may find that it says something like:

exchange_mode aggressive;

If so, see if you can change it so that it uses main-mode:

exchange_mode main;

Next, disable the built-in launchd script that launches racoon normally:

sudo launchctl unload /System/Library/LaunchDaemons/com.apple.racoon.plist

Then, you can temporarily launch racoon, and instruct it to use the configuration file that you exported:

sudo racoon -f ~/Desktop/vpn.aec.com.br -l /var/log/racoon.log

The racoon process will run in the background using the configuration file that you copied onto the Desktop. The process will also output to /var/log/racoon.log Next, you can initiate a VPN connection using racoonctl:

sudo racoonctl vpn-connect vpn.aec.com.br

The VPN menubar item will not update while this process is connecting. However, you should see output in /var/log/system.log and in /var/log/racoon.log that reflects the fact that the IPSec Phase 1 connection is moving along (i.e., Main Mode Message 2, 3, 4, etc.). If you see that the machine is able to establish the IPSec tunnel (look for "IPSec Phase1 established" in system.log), you're likely having problems with the exchange_mode that's configured.

How to undo this configuration

To put things back to the way that they were, you can disconnect (if the connection was successful) and then terminate the racoon process that's running:

sudo racoonctl vpn-disconnect

sudo killall racoon

Then, re-load the launchd config for racoon:

sudo launchctl load -w /System/Library/LaunchDaemons/com.apple.racoon.plist

How to make this configuration permanent

If the racoon configuration file that you used in the tests above seems to be allowing phase 1 to complete, you can configure racoon to use that config file in the future:

Copy the config file that is on your Desktop into the folder /etc/racoon:

sudo cp ~/Desktop/vpn.aec.com.br.conf /etc/racoon/vpn.aec.com.br.conf

Make sure to secure the permissions on that file:

sudo chmod 600 /etc/racoon/vpn.aec.com.br.conf

Comment out the last line of the file at /etc/racoon/racoon.conf, and add a line that will load the configuration that you copied to /etc/racoon in the step above:

include "/var/run/racoon/*.conf" ;

Should be changed to:

#include "/var/run/racoon/*.conf" ;
include "/etc/racoon/vpn.aec.com.br.conf" ;

After you've made this change, you can save the file and attempt the VPN connection again from the menu bar.