Connect MacBook OS X to Work Microsoft VPN

If your company allows it, BYOD (Bring Your Own Device) to work could be a sweet idea. You could use your weapon of choice to plow through the daily grind. However, Apple / Linux users will need to find an alternative to get some Microsoft (widely used platform in corporate world) settings working properly on their devices, i.e. company VPN (Virtual Private Network) settings, particularly the authentication part.

The gist of our company VPN settings are as follows:

VPN Type: L2TP / IPsec with Pre-shared key
Username & password: Microsoft Active Directory
IP Settings: Do not use default gateway on remote network

Here’s what I did to configure these settings in my MBP:

1. Go to System Preferences > Network

2. Click + sign at the lower left corner of the window to start creating a new VPN interface.

Select VPN in the Interface box, and type in a name that makes sense to you in the Service name box.

3. I left the Configuration box with Default, and then I entered the Server Address and Account Name provided to me by our IT.

4. Click on the Authentication Settings… button, and chose which ever User Authentication method you need to use as advised by your ID. It was Password for my case.

Do the same for the Machine Authentication. As I’ve mentioned earlier, I needed to use Shared Secret.

Click OK.

5. Click on the Advanced… button > Options > put a check on Send all traffic over VPN connection, and then click OK.

6. Click on Apply to save all your settings.

7. Open Terminal app and type the following commands:

sudo touch /etc/ppp/options

Type in your password to allow creating a file named options inside /etc/ppp/

sudo vi /etc/ppp/options

This will open an editor to to put in the rest of the settings that we need to make the mac OS X VPN work with MS-CHAP. This might look intimidating but you should be just fine if you follow the next steps. Worst case, you won’t be able to edit the file and the VPN will not work. In other words, your MBP will not explode; so brave-up and follow me:

A. Press i on your keyboard (this will start Insert mode)

B. Type the following (one line each)


C. Press Esc key on your keyboard

D. Type :wq! and then press Enter / Return on your keyboard to save what we just did.

That’s it. Head back to System Preferences > Network and then connect to your VPN. Hope it works for you as well.


By |2018-10-07T12:56:15+00:00June 16th, 2017|Microsoft, Technology|0 Comments

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