Google Drive does work with a proxy server. However, it doesn't support authentication for those connections. For this to work seamlessly for your users, you can set up Google Drive as an authentication bypass.
Note: Setting up Google Drive as an authentication exception prevents easy user tracking of those domain hits. This is because the domains in question are very broad and other Google applications may use the same addresses.
- Add the Connect for Chromebooks category to Authentication exceptions, see our help topic, Creating authentication policies.
- Create a whitelist policy for the Connect for Chromebooks category, see our help topic, Creating web filter policies.
- Move this policy to the top of the Web filter policies table, see our help topic, Managing web filter policies.