From Sidebar links - Gmail Help:

Ads and Related Pages
Ads in Gmail are placed in the same way that ads are placed alongside Google search results and, through the Google AdSense program, on content pages across the web. The goal is to provide you with helpful ads, links and content relevant to your specific interests. Advertising and related information are displayed based on a completely automated process. [emph mine]

If it's automated, it's okay? Though that doesn't even explicitly mean that your privacy is protected -- an automated process could certainly fill a database full of some pretty compromising information from your emails. Heck, has anyone seen the search results AOL let slip in 2006? I'm not sure how I missed it, but I got the feeling that I'd never peered quite so intently through a keyhole into someone's most personal activities until I looked at some of those files. And they were, of course, created by an automated process.

But the implication, I think, is that the automation removes the personal connection. There is the feel of a double blind provided by the code between your personal email and corporations' ad copy.

From the page above's "Learn More" link:

Gmail is a technology-based program. Advertising and related information are shown using a completely automated process. Ads are selected for relevance and served by Google computers using the same contextual advertising technology that powers our AdSense program. This technology enables Google to target dynamically changing content such as email or daily news stories.

No humans will read the content of your email in order to target such advertisements or related information. Because the ads and related pages are matched to information that is of interest to you, we hope you'll find them relevant and useful.


Your Privacy

Google does not and will never rent, sell or share information that personally identifies you for marketing purposes without your express permission. No email content or other personally identifiable information will be provided to advertisers. [again emph mine]

No humans will read your emails? So now we won't even promise that humans won't be reading the key terms from your emails? Makes sense from a software engineering bias, but not from one of personal privacy.

Neither automation nor collective ("non-personal") data eliminate threats to privacy. This, unfortunately, hasn't yet stopped me from using Gmail.

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