In theory, the answer could be yes. Christopher Nguyen, who was earlier responsible for Google Apps operations at Google, shared this on Quora:
" A small number of GMail related engineers have access to the servers as a matter of necessity to do their jobs; a very small number of people actually access the contents as a matter of necessity to do their jobs, and even then, almost always only the associated metadata.
The rest have to file a request and justify any access they ever need, which is extremely rare. All have to sign paperwork re users’ privacy at the risk of dismissal & legal action, knowing that whatever they do is discoverable. And ultimately, an internal culture of respecting users’ privacy helps keep one another in check."
Google also serves contextual text ads in Gmail and these ads are triggered based on the content of the email message that your currently reading. Obviously it is the bots that are scanning your Gmail messages for relevant keywords but Microsoft, with a hope that some Gmail users will shift to Hotmail, is using this point to target Google on privacy.
" Some email services, like Gmail, actually read the contents of your mail (both sent and received, even if you aren’t a Gmail user but just sending to someone who is) in order to decide what kind of ads to serve up to you. They may call it “scanning” and attempt to equate it with less invasive activities like “checking for spam” but it’s quite different. For you, and the people you send mail to, it’s not spam, it’s personal."
Microsoft has also released a video, titled the Gmail Man, highlighting this Gmail behavior. Microsoft uploaded the video to YouTube, a platform owned by Google, and it isn’t therefore surprising that the video has garnered more dislikes than likes – after all, most YouTube users are also Gmail users and they aren’t buying Microsoft’s argument.
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