OpenConnect VPN on Mac OS X

openconnect.md

Unfortunately, the Cisco AnyConnect client for Mac conflicts with Pow. And by "conflicts", I mean it causes a grey-screen-of-death kernel panic anytime you connect to the VPN and Pow is installed.

As an alternative, there is OpenConnect, a command-line client for Cisco's AnyConnect SSL VPN.

Here's how to get it set up on Mac OS X:

1. OpenConnect can be installed via homebrew:

    brew update
    brew install openconnect
   

2. Install the Mac OS X TUN/TAP driver

3. (Optional) Running openconnect requires sudo, presumably because it affects resolution of DNS. So, I added password-less sudo ability for the openconnect command.

    sudo visudo -f /etc/sudoers
   

And added this line:

    %admin  ALL=(ALL) NOPASSWD: /usr/local/bin/openconnect

4. (Optional) When connecting to your SSL VPN, openconnect may complain about a "self-signed certificate" being in the chain and force you to explicitly accept it every time. The self-signed cert is actually the root certficate and (hopefully) is one with implicit trust (i.e. trusted by browsers), so we can safely trust it by specifying the CA file after exporting it from KeyChain:

5. Determine the name your root certificate (i.e. visit your SSL VPN in Chrome, click the green lock, click "Certificate Information")

6. Open the Keychain Access App

7. Search the "System Roots" keychain to find your root certificate and select it

8. File > Export Items... the certificate as a .pem file somewhere on your hard drive (I put it in ~/.ssh/<certificate name>.pem

9. Connect!

    sudo openconnect --user=<VPN username> --cafile=<.pem file from step 4.3> <your vpn hostname>
   

   The only thing you should be prompted for is your VPN password. I added the command to my aliases file.

10. To disconnect, just Ctrl-c in the window where you started the VPN connection.

Note

I had an incident after an unclean VPN exit where later the VPN hostname could not be found. I guess the DNS resolver was messed up. I was forced to reboot to fix it so I could reconnect to the VPN.

Hi @choodique The open connect CLI supports two options, token-secret and token-mode which will let you enter a second password assuming it's based around a common method of 2FA. For a typical totp code (like you'd use with google authenticator on your phone), you'd add the following: --token-mode=totp --token-secret=base32:$VPN_TOTP_SECRET
...

In my situation, "Password" and "Second password" are identical and must be set at the same time.
Because of this echo MyPassword before openconnect... command doesn't work =(

I've created a shell script (https://github.com/sorinipate/vpn-up-for-openconnect) that automates some of this stuff. I hope it helps!

Use security to store and retrieve passwords from your Keychain if you use that as password manager: https://www.netmeister.org/blog/keychain-passwords.html

I use security find-generic-password -a myuser -s "mydomain" -w | sudo openconnect --passwd-on-stdin ... which removes the extra password prompt.

there is just one big issue with openconnect, if you kill the process via "Activity Monitor", it messes up with networking. nothing works! LAN and WiFi.

is there any way to fix the networking issue after killing the process? I'm using Applescript to automate connection. sometimes openconnect stops working and all I can do is killing it via Activity Monitor.

Did you ever figure this out? I’m in this exact same scenario. It was working then I got disconnected from inactivity then my WiFi doesn’t work anymore

there is just one big issue with openconnect, if you kill the process via "Activity Monitor", it messes up with networking. nothing works! LAN and WiFi.
is there any way to fix the networking issue after killing the process? I'm using Applescript to automate connection. sometimes openconnect stops working and all I can do is killing it via Activity Monitor.

Did you ever figure this out? I’m in this exact same scenario. It was working then I got disconnected from inactivity then my WiFi doesn’t work anymore

Same for me unfortunately. WiFi connects and I can access other resources inside the network, but internet connection is just broken. Rebooting does not fix the issue.
I'm on Sonoma 14.4.1

Only problems I have are usually DNS-settings related. I have a script that clears all DNS-settings on all interfaces. Usually that solves my problems.

Only problems I have are usually DNS-settings related. I have a script that clears all DNS-settings on all interfaces. Usually that solves my problems.

Worked like a charm. Thank you for the quick reply.

why after installing openconnect by brew install, the openconnect is command not found. Do u come across the same issue?

why after installing openconnect by brew install, the openconnect is command not found. Do u come across the same issue?

probably a PATH issue