Hacker News Reader

Comment by oconnore | Hacker News Reader

The assumption he implicitly makes is that Google is not going to do anything malicious with his password, and has a secure enough network. If you take this assumption to be true, then his practice of emailing himself private information (over SSL, you can't access gmail without it), is reasonable.

Now if you want to take issue with his assumption, then go right ahead, but this is not an instance of Jeff Atwood misunderstanding how [eg]mail works.

View on HN

The only reason for this would be that gmail -> gmail email doesn't leave their servers. However, I think it's irresponsible to suggest emailing oneself private information without explaining the caveat, because others might, say, do the same thing from their work email to their gmail account, and consequently send private data in the clear through random mail servers.

The GMail smtp service supports STARTTLS for incoming mail. It could very well be encrypted every single hop, from sending client to origin SMTP relay, from SMTP relay to GMail, and then from GMail to receiving IMAPS client.

The situation is a lot better than it was a handful of years ago. It's not quite the "don't ever do this!" it once was.

It doesn't just support it, it requires it.

GMail does not require STARTTLS.

I am sure you can send email to GMail accounts with unencrypted SMTP. Just look at the incoming "Received" headers. If they do not contain a "cipher=" section, the connection was not encrypted.

I think what you mean is that GMail requires you to use https for their web interface.

I think what you mean is that GMail requires you to use https for their web interface.

gmail requires STARTTLS (or ssmtp) when an authenticated user submits outbound mail to them via SMTP (http://support.google.com/mail/bin/answer.py?hl=en&answe...), which is what he may have been mis-remembering. But, yes, it is incorrect that all mail sent to gmail.com addresses is TLS encrypted.

I feel kinda dirty sticking up for Jeff here - but that means if you _know_ your outbound mail always uses TLS when available, then maybe the security-in-transit concerns are eliminated. (I don't even know where I'd start trying to find out if all my possible ways of sending myself mail can be conclusively determined to be using TLS though.)

That would be a perfect counter argument, except the point mentioned in the article specifically related to getting passwords sent to you from other services.

> GMail does not require STARTTLS.

    $ telnet smtp.gmail.com 587
    Trying 173.194.67.108...
    Connected to gmail-smtp-msa.l.google.com.
    Escape character is '^]'.
    220 mx.google.com ESMTP ea6sm27303065wib.5
    HELO zwp
    250 mx.google.com at your service
    AUTH PLAIN [elided]
    530 5.7.0 Must issue a STARTTLS command first. ea6sm27303065wib.5



    $ telnet smtp.gmail.com 587 
    Trying 173.194.67.109...
    Connected to gmail-smtp-msa.l.google.com.
    Escape character is '^]'.
    220 mx.google.com ESMTP ff2sm43397967wib.9
    HELO zwp
    250 mx.google.com at your service
    MAIL FROM:<test@example.com>
    530 5.7.0 Must issue a STARTTLS command first. ff2sm43397967wib.9

Please try your test again on port 25, which is the port that server-to-server e-mail would use, as the post above yours said that it is possible to send e-mail to @gmail.com without using STARTTLS. This is, in fact, not only possible but required. Otherwise, @gmail.com would be inaccessible to any e-mail address using an MTA that does not support or is not configured for TLS.

This is outgoing SMTP. It does not require it for _incoming_ SMTP.

Gmail recommends (or requires) SSL for both IMAP[1] and POP[2].

[1] http://support.google.com/mail/bin/answer.py?hl=en&answe... [2] https://support.google.com/mail/bin/answer.py?hl=en&answ...

"The assumption he implicitly makes is that Google is not going to do anything malicious with his password … "

Not necessarily "malicious" - I wonder if I could set up some adwords targeting keywords out of the popular passwords from the various lists of exposed passwords (Gawker, Sony, RockYou, etc), and attempt to social engineer people to give me "just" their passwords on my landing pages... I wonder if I had an unusual password, perhaps "incandescent-frog", in my email archive - could an advertiser "detect" that from me clicking an ad?

>The assumption he implicitly makes is that Google is not going to do anything malicious with his password, and has a secure enough network. If you take this assumption to be true, then his practice of emailing himself private information (over SSL, you can't access gmail without it), is reasonable.

No it's not. First, it's does have to be Google to do something malicious with your mail. An exploit, e.g XSS, could be found for Gmail any day --there were several in the past.

Second, was does "has a secure enough network" means? Does he only ever log on to Gmail from one network? The assumption of "secure enough network" and the words "hacker-proof" do no go together well.

Reply on news.ycombinator.com