We know that Chromebooks don't like having SSL inspection turned on but the following XG exceptions can be added to allow them to work. There's advice from Google here -
^([A-Za-z0-9.-]*\.)?1e100\.net1/
^([A-Za-z0-9.-]*\.)?accounts\.google\.com/
^([A-Za-z0-9.-]*\.)?accounts\.google\.co\.uk/
^([A-Za-z0-9.-]*\.)?gstatic\.com/
^([A-Za-z0-9.-]*\.)?accounts\.youtube\.com/
^([A-Za-z0-9.-]*\.)?clients1\.google\.com/
^([A-Za-z0-9.-]*\.)?clients2\.google\.com/
^([A-Za-z0-9.-]*\.)?clients3\.google\.com/
^([A-Za-z0-9.-]*\.)?clients4\.google\.com/
^([A-Za-z0-9.-]*\.)?commondatastorage\.googleapis\.com/
^([A-Za-z0-9.-]*\.)?cros-omahaproxy\.appspot\.com/
^([A-Za-z0-9.-]*\.)?dl\.google\.com/
^([A-Za-z0-9.-]*\.)?dl-ssl\.google\.com/
^([A-Za-z0-9.-]*\.)?gvt1\.com/
^([A-Za-z0-9.-]*\.)?gvt2\.com/
^([A-Za-z0-9.-]*\.)?gvt3\.com/
^([A-Za-z0-9.-]*\.)?gweb-gettingstartedguide\.appspot\.com/
^([A-Za-z0-9.-]*\.)?m\.google\.com/
^([A-Za-z0-9.-]*\.)?omahaproxy\.appspot\.com/
^([A-Za-z0-9.-]*\.)?pack\.google\.com/
^([A-Za-z0-9.-]*\.)?policies\.google\.com/
^([A-Za-z0-9.-]*\.)?safebrowsing-cache\.google\.com/
^([A-Za-z0-9.-]*\.)?safebrowsing\.google\.com/
^([A-Za-z0-9.-]*\.)?ssl\.gstatic\.com/
^([A-Za-z0-9.-]*\.)?tools\.google\.com/
^([A-Za-z0-9.-]*\.)?googleapis\.com/
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