Gmail shows authentication data to the recipient

Yesterday Gmail rolled out some changes to their interface. One of the changes is that they are now showing end users authentication results in the user screen.
It’s really the next step in email authentication, showing the results to the end user.
So how does Google do this? Google is checking both SPF and DKIM. If mail is authenticated and the authentication matches the from address then they display the email as:
mail from steve to me
If we click on “details” for that message, we find more specific information.
full details of message showing signing domain and spf domainIn this case the mail went through our outgoing mailserver to gmail.
Mailed-by indicates that the message passed SPF and that the IP address is a valid source of mail from wordtothewise.com.
Signed-by shows the domain in the DKIM d=. In this case, we signed with the subdomain dt.wordtothewise.com. That’s what happens when you sign using the domain in the From address (or a subdomain of it).
For a lot of bulk senders, though, their mail is signed using their ESP’s domain instead.  In that case Gmail shows who signed the mail as well as the from address.

And when we click on “details” for that message we see:
3rd party signature detailsThis is an email from a sender using Madmimi as an ESP. Madmimi is handling both the SPF authentication and the DKIM authentication.
As an aside, this particular  sender has a high enough reputation that Gmail is offering me an unsubscribe option in their interface.
Gmail is distinguishing between first party and third party signatures in authentication. If the mail is authenticated, but the authentication appears to be handled by a separate entity, then Gmail is alerting recipients to that fact.
What does this mean for bulk senders?
For senders that are signing with a domain that matches their From: domain, there is no change. Recipients will not see any mention of your ESP in the headers.
However, if you are using an ESP that is signing your mail with a domain they own, then your recipients will see that information displayed in the email interface. If you don’t want this to be displayed by Gmail, then you will need to move to first party signing. Talk to your ESP about this. If they’re unsure of how to manage it, you can point them to DKIM Core for an Email Service Provider.
Gmail blogpost about the changes
Gmail help page about authentication results

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Predictions for 2008

I did not have a lot of predictions for what will happen with email at the beginning of the year so I did not do a traditional beginning of the year post. Over the last 3 – 4 weeks, though, I have noticed some things that I think show where the industry is going.
Authentication. In January two announcements happened that lead me to believe most legitimate mail will be DK/DKIM signed by the end of the year. AOTA announced that approximately 50% of all email was currently authenticated. They did not separate out SPF/SenderID authentication from DK/DKIM authentication, but this still suggests email authentication is being widely adopted. AOL announced they will be checking DKIM on their inbound mail. I expect more and more email will be DKIM signed in response to this announcement.
Filtering. The end of 2007 marked a steady uptick in mail being filtered or blocked by recipient domains. I expect this trend to continue throughout 2008. Recipient domains are rolling out new technology to measure complaints, evaluate reputation and monitor unwanted email in ways that tease out the bad actors from the good. This means more bad and borderline email will be blocked. Over the short term, I expect to see more good email blocked, too, but expect this will resolve itself by Q2/Q3.
Sender Improvements. As the ISPs get better at filtering, I expect that many borderline senders will discover they cannot continue to have sloppy subscription practices and still get their mail delivered. Improved authentication and better filtering let ISPs pin-point blocks. Instead of having to block by IP or by domain, they can block only some mail from a domain, or only some mail from an IP. There are a number of senders who are sending mail that users do not want mixed with mail that recipients do want. Right now, if there is more mail that recipients want in that mix, then ISPs let the mail through. This will not continue to happen through 2008. Senders will need to send mail users actively want in order to see good delivery.
Less is more. A lot of other email bloggers have talked about this, and I will echo their predictions. Less email is more. Send relevant mail that your customers want. Target, target, target. Good mailers will not send offers to their entire database, instead they will send mail to a select portion of their database.
Feedback loops. Use of feedback loops by recipient domains will continue to grow.
Mobile email. More recipients will be receiving email on mobile devices.
Suggestions for 2008

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What is Two Factor Authentication?

Two factor authentication, or the snappy acronym 2FA, is something that you’re going to be hearing a lot about over the next year or so, both for use by ESP employees (in an attempt to reduce the risks of data theft) and by ESP customers (attempting to reduce the chance of an account being misused to send spam). What is Authentication?
In computer security terms authentication is proving who you are – when you enter a username and a password to access your email account you’re authenticating yourself to the system using a password that only you know.
Authentication (“who you are”) is the most visible part of computer access control, but it’s usually combined with two other A’s – authorization (“what you are allowed to do”) and accounting (“who did what”) to form an access control system.
And what are the two factors?
Two factor authentication means using two independent sources of evidence to demonstrate who you are. The idea behind it is that it means an attacker need to steal two quite different bits of information, with different weaknesses and attack vectors, in order to gain access. This makes the attack scenario much more complex and difficult for an attacker to carry out.
It’s important that the different factors are independent – requiring two passwords doesn’t count as 2FA, as an attack that can get the first password can just as easily get the second password. Generally 2FA requires the user to demonstrate their identity via two out of three broad ways:

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DKIM "i=" vs "d=" and Reputation

This really should be part seven of a twelve part series or some such as it deals with an aspect of DKIM that’s really important, but is way down in the details of implementation. (dkim.org is a reasonable place to start for a general overview of DKIM).
There’s an apparently endless thread on the DKIM-SSP spec development mailing list at the moment about the differences between two fields in a DKIM signature that could be used to tie a senders reputation to. Several ESP delivery folks asked me to explain what everyone was talking about, and this post is a first cut at that.
“i=” vs “d=”
There are two possible fields in a DKIM signature that could be used to identify the sender of a message, and so to tie a sender history and reputation record to. They are the so-called “i=” and “d=” field, from the syntax used to include them in the signature.

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