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Chromebooks and SSL Interception

1 min read

Summary #

If you are currently using Google Chromebooks with Transparent filtering and you want to use SSL Intercept, you will need to configurethe Chromebooks to use the WAPD Automatic configuration script. Google does not recommend that you use aTransparent Proxy with SSL inspection.

https://support.google.com/chrome/a/answer/3504942?hl=en

More Information #

First, you must have the following setup and configured before you begin.

  1. Contact K12USA so we can enable the wpad.dat file to be used from outside the local network and to supply you with the K12USA hostname for your SecureSchool appliance. (ex. secureschool.domain.nj.k12us.com)

Chrome Management Settings #

  1. Login to the Google Apps Admin Console,Select the Chrome Management
  1. Then select User Settings.
  1. Change the following settings:
    1. Network – Proxy Settings – Always use proxy auto-config specified below
    2. Proxy Server Auto Configuration URL – http://secureschool.domain.nj.k12us.com:81/wpad.dat
    Specify the K12USA hostname for your SecureSchool appliance. Confirm that the name can resolve to the correct IP address when inside the network (internal IP address of SecureSchool) and outside the network (external IP Address of SecureSchool) on port 81.(important)
  2. When you are done click on the “Save Settings”button on the bottom of the screen and then you can log out of theGoogle Apps Admin Console.
  3. To confirm that the device is getting the latest policy or to reload the policy, on the device open the browser and go to: chrome://policy
  4. To confirm that proxy settings are in effect,on the device open the browser and go to: chrome://net-internals/#proxy
  5. Test – Open a website that should be blocked and you should see the “Access Denied” page for your school.

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