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I ask because I connect to Gmail over HTTPS and if emails sent from one account to another (or the same account, just to back something up) don't actually leave Google then it's end-to-end email encryption. Is this the case?

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If you are that concerned over privacy, then you should not be using email as backup. – Keltari Aug 23 '11 at 23:02
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Nothing ever leaves Google, it records the entire Internet and everybody on it! – Moab Aug 23 '11 at 23:29
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1 Answer

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It depends on the network setup Google has. You can check the route your email took by checking the message headers. In GMail, you can do this by[1]:

  1. Log in to Gmail
  2. Open the message you'd like to view headers for.
  3. Click the down arrow next to Reply, at the top of the message pane.
  4. Select Show Original.

Look for the Received headers. Those identify the email servers that handled the email.

However, to completely ensure that you have end-to-end privacy, you should encrypt you email using PGP or GNUPG.

Source: [1] https://mail.google.com/support/bin/answer.py?answer=22454

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I'm getting 2 received headers both containing private (10.*.*.*) addresses so I guess it's not going far... – Matt Aug 23 '11 at 23:08
Yeah, I guess Google's SMTP servers keep it in house. Although, depending on the level of privacy you need, third parties can still access email on GMail server, via subpoena, [puts tinfoil hat on]NSA bugs[hat off] etc. – Nithin Philips Aug 23 '11 at 23:13
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>> ...don't actually leave Google then it's end-to-end email encryption. End-to-end encryption means that the message is encrypted from the time it leaves the sender until it arrives at the recipient. Even if the email does not leave Google's 'network' it is not encrypted while it is stored, just while it is transferred from sender to server and server to receiver. As Ninthin wrote, if you want to end-to-end encryption, you should use an encryption package. GPG, PGP, TrulyMail, or another. There are many (and some are free) but you need to get counterparty agreement on the software to use. – John Aug 28 '11 at 3:09
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