Hacker News Board Hacker News, browsed like a classic message board
Live data from Hacker News

Gmail Will Warn If Message Is Not Authenticated/Encrypted

gmailblog.blogspot.com

Post reply on HN
Print view View original

81–90 of 216 posts

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#81

Post by elihu »

emergentcypher wrote: post #41
jcoffland wrote: post #30

This sounds great but Google has been making it harder and harder to run your own mail server even for personal use. I think they would be happy of email servers were only run by a few large companies. They make it sound like they are doing the right thing but really they are bully the industry to do it their way. So many people have Gmail accounts that you can't run an email server that cannot send email to Google.…

Now I can just get a free cert and turn on TLS. What's the problem, exactly? Most people are not capable of running their own mail server. The convenience of services like Google, plus the risk of turning your mail box into a spam machine, vastly outweighs the downsides for most people.

> What's the problem, exactly?

> Most people are not capable of running their own mail server.

I think that is a big part of the problem. It should be relatively straightforward for someone who isn't a full-time email server administrator to setup a mail server correctly, but it's not. At least, it wasn't easy last time I tried it with Postfix and (iirc) Courier on Ubuntu. All the cryptography options are disabled by default and you have to spend a lot of time figuring out which ones should be turned on, where to stick the certificate files and how they should be formatted, how to get Courier and Postfix to talk to each other, etc...

Maybe there's an easy solution (besides "pay someone a monthly fee to manage this all for me") that I'm oblivious to, but it seemed like I was on a well-travelled path and it was a lot harder than it should have been.

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#82

Post by mynameisvlad »

Navarr wrote: post #80
jcoffland wrote: post #30

This sounds great but Google has been making it harder and harder to run your own mail server even for personal use. I think they would be happy of email servers were only run by a few large companies. They make it sound like they are doing the right thing but really they are bully the industry to do it their way. So many people have Gmail accounts that you can't run an email server that cannot send email to Google.…

These aren't requirements. Gmail is a mail client. What it is doing is adding warnings. Without SPF/DKIM you can't be authenticated. Google is showing the user that they cannot verify the sender. Without TLS email is sent in the clear. Google is showing the user that sensitive information will be visible when sent over the network. You can run your server fine without this, but users will be warned that you're not fo…

> These aren't requirements

Well, except they are. Before, yes, they were just best practices. It was great if you had them but by no means required and didn't really impact your experience much if at all. With this switch, though, they became requirements to getting a "normal" experience in Gmail. Even having a warning is a degraded experience at this point.

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#83

Post by pera »

emergentcypher wrote: post #41
jcoffland wrote: post #30

This sounds great but Google has been making it harder and harder to run your own mail server even for personal use. I think they would be happy of email servers were only run by a few large companies. They make it sound like they are doing the right thing but really they are bully the industry to do it their way. So many people have Gmail accounts that you can't run an email server that cannot send email to Google.…

Now I can just get a free cert and turn on TLS. What's the problem, exactly? Most people are not capable of running their own mail server. The convenience of services like Google, plus the risk of turning your mail box into a spam machine, vastly outweighs the downsides for most people.

My first concern is, if nowadays is so easy to get your certs signed by a CA how can "Authenticated/Encrypted" emails successfully prevent phishing attacks? In my modest opinion there are many week points in X.509 and how CAs are verifying identities, and even if this things were fixed you still have the problem of state-sponsored attacks that have no solution within the current www pki. I personally have no problem if Google wants to add some icon in the UI, but I share OP's concerns.

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#84

Post by linkregister »

hueving wrote: post #54
emergentcypher wrote: post #41

Earlier quoted context omitted.

Now I can just get a free cert and turn on TLS. What's the problem, exactly? Most people are not capable of running their own mail server. The convenience of services like Google, plus the risk of turning your mail box into a spam machine, vastly outweighs the downsides for most people.

>Now I can just get a free cert and turn on TLS. What's the problem, exactly? Certs weren't free for business use until let's encrypt.

Long before Let's Encrypt, SMTP transactions with STARTTLS have permitted self-signed and non-root-CA chained certificates.

The pervasiveness of self-signed certificates for SMTP servers means that rejecting them would drop large amounts of email. STARTTLS is basically useful for thwarting passive collection of network traffic.

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#85

Post by magila »

KirinDave wrote: post #76
jcranmer wrote: post #64

Unfortunately, this is the sort of a change that's a red herring for any actual improvements to email security. The use of unencrypted or encrypted link to the receiving email provider's MX server doesn't change all that much in terms of who can read the email: it's still sitting in plaintext on the recipient's server (as well as the sender's server), and the group of actors who can sniff traffic on the backbone like…

> The use of unencrypted or encrypted link to the receiving email provider's MX server doesn't change all that much in terms of who can read the email: it's still sitting in plaintext on the recipient's server (as well as the sender's server), and the group of actors who can sniff traffic on the backbone like that is probably just as easily able to get it from the servers. That's not at all obvious to me. And this so…

A state actor who can sniff traffic can just as easily serve a secret order to the email server operator to compel them to hand over the data. In fact this is already SOP for governments when dealing with communications which are encrypted in-flight but not end-to-end.

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#86

Post by jms703 »

jcoffland wrote: post #30

This sounds great but Google has been making it harder and harder to run your own mail server even for personal use. I think they would be happy of email servers were only run by a few large companies. They make it sound like they are doing the right thing but really they are bully the industry to do it their way. So many people have Gmail accounts that you can't run an email server that cannot send email to Google.…

> Google has been making it harder and harder to run your own

insecure mail server

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#87

Post by Navarr »

kps wrote: post #20
lstamour wrote: post #18

Earlier quoted context omitted.

Gmail uses an associated Google+ profile for authenticated emails, so you need both for it to work going forward, I presume. To get started, check https://www.google.com/business/ Outlook uses Facebook and Twitter, if you have these contacts integrated. Yahoo does this too: http://techcrunch.com/2015/03/04/smart-contact-cards-arrive-... There really should be some kind of standard or mail header though. :) Come to th…

> There really should be some kind of standard or mail header though. :) https://en.wikipedia.org/wiki/X-Face

X-Image-URL is neat - but how do we trust it? Ensure the header is DKIM signed?

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#88

Post by sinatra »

I think as HNers, we're focusing too heavily on niche cases (like running your own email server). But, for general public who is still sharing their own (and more importantly, their clients') SSNs, passwords, and other very sensitive information on email, this may be the trigger that educates / trains them to be more careful. I am definitely looking at this as a positive.

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#89

Post by pera »

tantalor wrote: post #37
jcoffland wrote: post #30

This sounds great but Google has been making it harder and harder to run your own mail server even for personal use. I think they would be happy of email servers were only run by a few large companies. They make it sound like they are doing the right thing but really they are bully the industry to do it their way. So many people have Gmail accounts that you can't run an email server that cannot send email to Google.…

> some new technology that Gmail demands > everyone is going to switch, now The article is pretty clear that gmail users can keep emailing others who don't support TLS or authentication; they will just now see an additional icon informing them of that condition. Nobody is being demanded to switch anything. disclaimer: works for Google

Hi there, I have two questions: first, which CAs will you use? and second, what will you do when a CA gets compromised? Thanks!

Re: Gmail Will Warn If Message Is Not Authenticated/Encrypted

#90

Post by Navarr »

ecthiender wrote: post #53

There are really good, albeit few, alternatives: Fastmail ( https://www.fastmail.com/ ) Tutanota ( https://tutanota.com/ ) Riseup ( https://help.riseup.net/ )

I would be surprised if Fastmail didn't adopt similar policies.

These are good-for-the-user policies.

Post reply on HN