If TLS inspection isn't working verify that the hostname whitelist is working
- Boot up and sign in to your Chromebook or login as guest.
- Use the keyboard shortcut Ctrl + Alt + T to open the Crosh terminal in your browser.
- Type:
network_diag --hosts
or, if you use a HTTP proxy:
network_diag --hosts --proxy http://192.168.1.1:8888
where http://192.168.1.1:8888 is the hostname and port of your HTTP proxy.
The command will attempt a TLS connection to each of the hosts in the whitelist and report PASS / FAIL. If all hosts are not passing, check your firewall / proxy to confirm the host is properly whitelisted.
Sample command and output:
crosh> network_diag --hosts
checking accounts.google.com... PASS
checking accounts.gstatic.com... PASS
checking accounts.youtube.com... PASS
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