Jose Jimenez
Jose Jimenez
Software Architect & Developer
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Installing Homebrew and Using OpenConnect on Mac with shell to Manage VPN

Published in VPN on Aug 29, 2023


In this blog post, we will guide you through the process of installing Homebrew, a package manager for macOS, and using OpenConnect to manage your VPN connections. Specifically, we will focus on executing a command to establish a VPN connection using OpenConnect on your Mac.

Step 1: Installing Homebrew

Homebrew simplifies the process of installing and managing command-line tools and software packages on macOS. Follow these steps to install Homebrew:

  1. Open the Terminal application on your Mac.
  2. Paste the following command and press Enter:
1/bin/bash -c "$(curl -fsSL"
  1. Follow the instructions provided during the installation process.
  2. Once Homebrew is installed, you can verify its installation by running the following command:
1brew --version

Step 2: Installing OpenConnect

OpenConnect is an open-source software that enables users to establish SSL VPN (Virtual Private Network) connections. To install OpenConnect using Homebrew, perform the following steps:

  1. Open Terminal and execute the following command to install OpenConnect:
1brew install openconnect
  1. Homebrew will download and install OpenConnect and any required dependencies.

Step 3: Configuring VPN Connection using OpenConnect
Now that we have installed both Homebrew and OpenConnect, we can proceed with configuring and connecting to your VPN. Here's the command to connect to your VPN using OpenConnect:

1cat ~/.vpnpw | sudo openconnect xx.xx.xx.xx --protocol=anyconnect --user=jose --authgroup=vpn --passwd-on-stdin --servercert SERVERCERT

Let's break it down:

  • cat ~/.vpnpw: This command reads the contents of the .vpnpw file, which typically stores your VPN password.
  • sudo openconnect: The sudo command allows you to execute the subsequent command with administrative privileges. OpenConnect is the command used to establish the VPN connection.
  • xx.xx.xx.xx: Replace this with the hostname or IP address of your VPN server.
  • --protocol=anyconnect: Specifies the VPN protocol to be used. In this case, we are using the AnyConnect protocol.
  • --user=jose: Provide your VPN username.
  • --authgroup=vpn: Specifies the authentication group to connect to.
  • --passwd-on-stdin: Reads the VPN password from the standard input.
  • --servercert SERVERCERT: If required, specify the path or name of the VPN server certificate.

Make sure to replace the necessary information with your own credentials and server details.

Disconnecting or terminating VPN connection

To disconnect or terminate the VPN connection established using OpenConnect, you can advise the user to follow these steps:

  1. Open Terminal on your Mac.
  2. Press Ctrl + C to interrupt the current running command and terminate the VPN connection.
  3. If prompted, enter the administrator password to complete the termination process.

By following these steps, the user will effectively kill the VPN connection and disconnect from the VPN server.


Congratulations! You have successfully installed Homebrew and OpenConnect on your Mac. Additionally, we have walked through the steps to configure and connect to your VPN using the OpenConnect command. With these tools in place, you can now easily manage your VPN connections on your Mac.