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I searched for websites with a keyword, say, "Monkey", using HTTPS-enabled Google Search on my company's machine.

Can the network administrator somehow associate with me:

  1. The keyword "Monkey"?
  2. The URLs of the searched websites containing the keyword "Monkey"?
  3. The contents of the above websites?
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    I think it depends less on Google and more on your network’s configuration. – Alex Feb 23 '16 at 16:30
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When you access any site via HTTPS, everything but the server's domain name gets hidden from anyone between your browser and the server.

In your case, your search used a URL like

https://www.google.com/search?q=monkey

(most likely with more name-and-value query parameters like &name=value)

All your network administrator can tell is that you made an https request to www.google.com. She doesn't even knows you went to /search, let alone the query parameters.

The content returned by Google was cryptographed. She couldn't see it (but she could have a general idea of its size).

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    Although the "company's machine" could have had any kind of remote desktop/monitoring software running undetected in the background. It could be monitoring browser history (and sending this to another server). It could even be monitoring keystrokes entered into certain applications. :/ – MrWhite Feb 23 '16 at 23:28

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