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Comment by tptacek | Hacker News Reader

It's not directly apropos this particular thread, but Google has engineered an email service that is particularly difficult to wiretap. To wit:

(a) They're the Internet's foremost adopter and proponent of DHE ciphersuites, which drastically reduce the impact of losing the RSA key that underpins most site's TLS security, and, just as importantly, forces adversaries to actively MITM every connection in order to decrypt them.

(b) They're a pioneer in key pinning, which bakes the identity of their key into the Chrome browser binary, meaning that when your Chrome browser talks to Google's mail service, it's unlikely to trust any otherwise- valid- looking certificate presented by a MITM attacker.

Google's mail service is better encrypted than most banks.

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Difficult to wiretap in the sense of intercepting communications to and from Google, yes.

But it's also engineered to give Google itself access to your data so they can improve their behavioral profile of you.

I think what people are suggesting is that if end user privacy was Google's priority rather than gaining access to user data for their own use, they could engineer a service that didn't place themselves as a man-in-the middle.

They're a pioneer in key pinning, which bakes the identity of their key into the Chrome browser binary, meaning that when your Chrome browser talks to Google's mail service, it's unlikely to trust any otherwise- valid- looking certificate presented by a MITM attacker.

Chrome doesn't pin actual certificates, just public keys of CAs. If some organization had access to Verisign, Equifax or Geotrust keys, they could just create new certificates for *.google.com, which Chrome would accept.

Am I right that a) applies only to direct communications between the end user and Google's servers?

Actually if someone sends an email to my Gmail account using his ISP SMTP server, is the connection between the two SMTP servers likely to be encrypted?

Even if it is encrypted, I doubt it's authenticated.

Wiretaps almost never involve active MITM. This is a red herring.

In these particular instances, though, information is much more valuable than money.

No, I don't believe that's true. The information in your mail is not more valuable to Google than the integrity of a bank account is to a bank.

Google has a financial interest in having access to the content of mail messages, but (a) it's an interest "in the large", not in any specific account, and (b) it's a nonrivalrous interest.

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