Secure Remote Access — BSD VPN — Step-by-step Installation Guide for Macintosh

*** BSD VPN access will be turned off on 3/1/22. Please use cVPN instead. ***

Note: If you intend to use the BSD VPN, you will need to enroll in DUO Two-Factor Authentication and register a qualifying device. This is a requirement for the BSD instance of VPN. Step-by-step instructions are available at University of Chicago Information Technology Services Knowledge Base: Two-factor Authentication.


How to install Cisco AnyConnect VPN Client manually on Mac OS

Before trying to run AnyConnect, Java must be installed and running on your computer. To enable Java, go to Finder > Go > Utilities > Java Preferences to trigger the install.

Note: Mac OS X 10.8 (Mountain Lion) and 10.9 (Mavericks) require you to disable “Gatekeeper.” Instructions for disabling Gatekeeper are available here.

Note: Mac OS X 10.9 (Mavericks) is not yet supported by the automatic installer at However, you could obtain the VPN software by following the directions here.

Mac OS X:

  1. Point your browser to
  2. Log in with your BSDAD Username and Password.
  3. The file will mount a disk image named “AnyConnect ” Open this disk image and launch the file named “AnyConnect.pkg.”
  4. On the “Install vpnclient” window, you will be prompted by the message: “This package will run a program to determine if the software can be installed…” Click Continue. Screen Capture of install step number 4
  5. On the following screen titled “Welcome to the vpnclient Installer”, click Continue again.Screen Capture of install step number 5
  6. When presented with the software license agreement, click Continue then click Agree on the slide-down menu.Screen Capture of install step number 6.1 Screen Capture of install step number 6.2
  7. On the window titled “Standard Install…” click Install and enter your computer username and password when prompted. (NOTE: the user must be an administrator of the machine to install).Screen Capture of install step number 7.1 Screen Capture of install step number 7.2 Screen Capture of install step number 7.3
  8. When the installation has completed, click Close.Screen Capture of install step number 8
  9. Cisco AnyConnect can be found in the Cisco folder located in the Application folder.Screen Capture of install step number 9
  10. Navigate to /Applications/Cisco/ and open “Cisco AnyConnect VPN Client”.
  11. In the “Connect to:” field, enter “” and click Connect.Screen Capture of install step number 11
  12. Enter your BSDAD username and password then click Connect. Screen Capture of install step number 12PLEASE NOTE: “Second Password” refers to the 6-digit numeric passcode generated by the DUO App on your phone. Alternatively, you can…
    Type the word “push” to get a notification through the DUO app on your phone -or-
    Type “sms” to send a text message to your phone -or-
    Type “phone” to get a phone call
  13. Upon successful connection, Cisco AnyConnect will minimize itself and you will see the AnyConnect logo with a small lock in your menu bar just to the left of the time.Screen Capture of install step number 13

Connecting after the program is installed:

To connect to the BSD VPN:

  1. Go to your Applications folder, then go to the Cisco folder, and then open the Cisco AnyConnect VPN Client program.
  2. In the box labeled Connect to, put
  3. Press the Select button if it is visible.
  4. In the box labeled Username, enter your BSDAD username (lowercase, no “”).
  5. In the box labeled Password, enter your BSDAD password.
  6. In the box labeled Second Password, enter one of the following DUO notification types for two factor authentication:
  7. Enter “push” for DUO push
  8. Enter “SMS” for text message
  9. Enter “phone’ for phone call
  10. Enter the DUO passcode on your phone
  11. Press the Connect button.
  12. When done with the VPN, quit the Cisco AnyConnect program or press the Disconnect button.