Chromebooks and SSL Interception


Summary

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

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

Applies To

SecureSchool, ISBossBox, LibraryDoor

 

More Infomation

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
2. Login to the Google Apps Admin Console, Select the Chrome Management
3. Then select User Settings.
4. Change the following settings:
a.) Network - Proxy Settings - Always use proxy auto-config specified below
b.) 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)

 

  5. When you are done click on the "Save Settings" button on the bottom of the screen and then you can log out of the Google Apps Admin Console.
6. To confirm that the device is getting the latest policy or to reload the policy, on the device open the browser and goto: chrome://policy
7. To confirm that proxy setting are in effect, on the device open the browser and gotochrome://net-internals/#proxy
8. Test - Open a website that should be blocked and you should see the "Access Denied" page for your school.