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What Gmail's New TLS Icon Really Means: Email Encryption Is Still Broken

An anonymous reader writes: On Safer Internet Day Google announced that Gmail will display warning signs for missing encryption and authentication, a great initiative indeed! Now that it's live we've taken it for a spin, only to find that the warning when composing email is quite slow (for new domains), and that they fail to mention that the non-authenticated TLS encryption that the currently sad state of SMTP encryption leaves us with is really poor, and vulnerable to almost anything (except passive wiretapping). I rather wish they took a stance on how we could move on to proper email encryption.

6 of 129 comments (clear)

  1. Crypto infrastructure is too frigging hard! by Anonymous Coward · · Score: 2, Insightful

    The problem here is that crypto infrastructure in general is too fucking hard for anyone but dedicated security professionals to work with. Hell, even they have a shitload of trouble with it, as we've seen from the many OpenSSL bug debacles lately! This technology is way beyond what average, or even above-average, computer users are capable of dealing with. Some people will probably reply saying, "But it's not that hard! I can understand it!", yet those are the kind of people who understand this technology the least. At least average computer users know crypto technology is way beyond their capabilities. These self-proclaimed "experts", on the other hand, don't realize how much they don't know! Until crypto becomes far more simpler for average folks to use then we just won't see it used.

  2. gmail is what has broken email. by Anonymous Coward · · Score: 5, Insightful

    I consider gmail to by my biggest threat to the privacy of my email.

    If I want end to end security, well there is a standard for that. I use it. It works.

    But gmail is close to having a monopoly on email. It isn't quite yet, but almost everyone I know uses exclusively gmail now. That means if I want to email them, Google IS the man in the middle. I can't easily email my friends without giving Google the contents of my email, which they will use to build a profile of me - and I've never signed up for any of their services or estasblished any kind of business relationship with them.

    Furthermore, most small to medium businesses are using gmail.

    Think about this: we used to have a decentralized, non-censorable, email standard that no one entity could control or pervert for their own ends. But the whole world said, "Fuck that, we want one advertising company to see everybody's email!.

    Google is the main threat to the privacy of email today. Like Bruce Schneier observed, they want you to have email privacy from everyone except them.

    1. Re:gmail is what has broken email. by sims+2 · · Score: 5, Insightful

      Well if anyone else had wanted to provide a reasonable amount of storage, allow attachments bigger than 4MB, provide both pop3 and imap access, not inject advertising into your outgoing mail, for "free".
      They could have been the largest email provider.

      But no one else wanted to do that for "free".

      --
      Minimum threshold fixed. Thanks!
  3. Wait, what? by s.petry · · Score: 4, Insightful

    Some of you will have a hard time with this, but... why is the problem here with SMTP? Is it really that hard to understand that MAIL TRANSPORT is not compatible with HIDE MY STUFF? Good grief people, you can't truly be that ignorant.

    Do you trust that anything you mail through the Post office, FedEX, UPS, or any other mail service is "Secure"? Do you believe it's impossible for people to know what's in your boxes because you use those services? I can provide you a list of drug dealers who thought so too, but they are jailed for that thought.

    Want secure, use secure. Lotus Notes was friggin awesome for securing content. Nobody wanted to pay for it though, and all the cool kids were using Outlook because you could drag-n-drop audio files right into your email (also read fart noises). Many Writing applications have encrypt/decrypt features. Zip has it too, but generic standard email? Come on now.. it's a MAIL TRANSPORT and works very well as a mail transport.

    If you somehow believe "Generic Transport" can also be "Secure", I got some ocean side property you may be interested in buying.

    --

    -The wise argue that there are few absolutes, the fool argues that there are no probabilities.

  4. This is going to be bad. by PAjamian · · Score: 4, Insightful

    Google is trying to force servers to use STARTTLS encryption for port 25 MX traffic, this is all commendable, but they are giving their users a false sense of security. When gmail does not display the broken padlock it simply means that the first hop to the recipient's MX server supports STARTTLS, but mail is routinely stored in plain text queues on multiple servers, transmitted on in additional hops that are not necessarily encrypted, and even the first hop encryption often times uses self-signed certs or certs signed by non-authoritative CAs, so the message being sent, while being encrypted is still vulnerable to man in the middle attacks.

    But Google is giving the impression that if that first hop offers STARTTLS, then the message will be sent securely and encrypted. This will result in people putting all sorts of credit card details and other information in their emails thinking (because Google said so) that the message is secure, when nothing could be farther from the truth.

    Google needs to stop this right away, it's going to do way more damage than good. There is only one way to hide the content of an email from prying eyes and that is with properly implemented PGP encryption. There is no way to hide the meta (envelope) data from prying eyes. It is really important that people not be misled on this account.

    --
    Windows is a bonfire, Linux is the sun. Linux only looks smaller if you lack perspective.
  5. Re:easy encryption by Anonymous Coward · · Score: 5, Insightful

    Imagine if you could actually write good clean documented code!

    Good example of how not to code.
    - no useful comments
    - the only two comments conflict with each other
    - no line breaks before "if" constructs or after "else" constructs
    - assumes existence of files for which it doesn't check existence
    - doesn't check status for execution of openssl commands

    Not bad for a six-year old.
    M