Mail Client Improvements

There’s been extensive and ongoing development of email through the years, but much of it has been behind the scenes. We were focused on the technology and safety and robustness of the channel. We’re not done yet, but things are much better than they were.
The good part of that is there is some space to make improvements to the inbox as well. Over the last few months there have been a number of announcements from different mail client providers about how they’re updating their mail client.

Unsubscribes handled by the email client

Apple announced they were adding a link to unsubscribe into the mail client for iOS 10. It works much like the links in the Gmail and Hotmail clients, by looking for the list unsubscribe header and then sending a message to that address. Al did a bunch of testing and has a full blog post on how the list unsub link works in iOS, so go check out his post.
The important bits are they’re only using the mailto: link, they are not following any URLs. For those of you who want to support this, you’ll need to provide an address for unsubscribes. One of the absolute easiest ways to do this is use an encoded left hand side of the address so each unsubscribe can be processed based on the email address. Think of it like a VERP string.
It’s worth noting that two large players, Apple and Google, in the email client space have focused on the mailto: link for unsubscribes. There are issues that come up with an email client mediated unsubscribes, but a number of them go away using a http:// level unsubscribe.
It’s also interesting that this innovation has created a discussion among some marketers about where the unsubscribe link should be in an email. Some people feel very strongly that the only right place to put an unsubscribe link is at the bottom of an email. That choice is being somewhat removed from their hands with these changes to the mail client.

Better CSS and HTML support

Last month Microsoft went to the Litmus design conference and announced they were going to be working with Litmus and email senders to improve mail display in Outlook. This week Gmail announced they were supporting more CSS to make responsive design easier.

Displaying security information to end users

Earlier this year, Gmail started showing their users if mail came in over an encrypted connection. Mail sent without using TLS received an open red padlock next to the sender’s name.
This week folks noticed Gmail had quietly rolled out another feature to communicate security status to end users. Now, if you click on “show original” Gmail doesn’t simply show you a raw text version of the file, they show you specific authentication information about that message.
I have a screen shot of what that information looks like.
GoogleShowOriginal
There are multiple features here that make it easier to see what’s going on with email.

  1. How long the delivery took! This is great, because there are so many places email can get caught up. This will tell senders wether the problem is on the sending side or the receiving side. Looking at the headers of this particular message, the time is looking at how long the message took to get from the Gmail MX to the user’s inbox (or, in this case, spam folder).
  2. SPF pass. The learn more link is a little disappointing, as it  mostly talks about how you can implement SPF, not about what it means for recipients. It also says it helps recipients distinguish spam, except this particular message is a classic 419 spam. But it’s a good start.
  3. DMARC pass. Again, there isn’t much information about why a user should care about DMARC passing in the learn more link, but it is a good start.

Overall, these are exciting developments for recipients and senders. It’s really nice to see some work being done at making mail clients more descriptive. Because so much online security revolves around email, it’s a critical security step to show authentication results to end users. I expect some of these changes will be pushed out to the inbox over time, as Gmail wrestles with providing enough but not too much information.
All in all, these are more meaningful changes to email clients than I’ve seen in years.

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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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