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Install and Run the Cisco AnyConnect client for VPN connectivity on Mac OS X including Duo

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  • This guide will assist with the installation of the Cisco AnyConnect VPN client for OS X 10.6 (Snow Leopard), 10.7 (Lion), 10.8 (Mountain Lion) and 10.9 (Mavericks).
  • You need administrator level account access to install this software.
  • Note: Some screen shots may be slightly different from what you see depending on the version of your operating system and the VPN software.


  1. Download the VPN installer from MIT's download page, Cisco AnyConnect Secure Mobility Client for MAC (certificates required).
  2. Find and open the downloaded file.
    Downloaded file

  3. The file will mount a disk image. Open this disk image and launch the file named "anyconnect-macosx-XXXXXX".

  4. On the following screen titled Welcome to the AnyConnect Secure Mobility Client Installer, click Continue.
    Welcome to installer screen

  5. When presented with the software license agreement, click Continue then click Agree on the slide-down menu.
    Software License agreement screen
    Agree to license screen

  6. If you are prompted "Select a Destination...", select your primary hard drive and click Continue.
  7. On the window titled Standard Install..., click the button labeled Install and enter your computer username and password when prompted and click Install Software.
    Note: The user must be an administrator of the machine to install.
    Standard installation message
    username and password prompt
    Result: The VPN client will begin to install itself.
    Installation progress bar
  8. When the installation has competed, click the button labeled Close.
    Installation successful screen

Initiating a Connection to VPN and to VPN using Duo

  1. Cisco AnyConnect can be found in the Cisco folder located in the Applications folder (/Applications/Cisco/).
    Cisco folder contents

  2. Navigate to /Applications/Cisco/ and open "Cisco AnyConnect Secure Mobility Client".
  3. To authenticate with Duo, enter and click the button labeled Connect.
    A second password

  4. Enter your MIT username and password then click the button labeled OK.
    Login screen

    With Duo authentication, you will see a field asking for a Second Password.
    Enter duo passcode

    In this field you may type in one of the following options:
    1. push - Duo will send a push notification to your registered cell phone with the Duo Security mobile app installed
    2. push2 - Duo will send a push notification to your _second registered device with the Duo Security mobile app installed_
    3. sms - Duo will send an SMS to your registered cell phone
    4. Phone -Duo will call your registered phone
    5. Phone2 -Duo will call your second registered phone
    6. Yubikey - If you are using a Yubikey for authentication, make sure the Second Password field is highlighted and use your key. For instructions on using the Yubikey, please see How do I authenticate with a YubiKey?
    7. The one time code generated by your hardware token or the Duo Security mobile app (the code changes every 60 seconds)

      In this example, I entered "push" in the Second Password field. I will receive a push notification on my cell phone, go to the Duo app and click Approve.
  5. When prompted at the MIT's Virtual Private Network (VPN) screen, click the button labeled Accept to connect to MIT's Virtual Private Network.
    Login screen

  6. 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.
    AnyConnect logo

IS&T Contributions

Documentation and information provided by IS&T staff members

Last Modified:

January 05, 2018

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