Gmail showing authentication info

Yesterday Gmail announced on their blog they would be pushing out some new UI to users to show the authentication and encryption status of email. They are trying to make email safer.
There are a number of blog posts on WttW for background and more information.

The short version is that TLS is encryption of the email between the sending server and the receiving server.  It means mail can’t be intercepted or changed while between one server and another.
Gmail is now showing users whether a mail was sent using TLS.
If a message is sent without using TLS, there is an open red lock shown.
Open red lock = unencrypted
If you hover over the open red lock, Gmail tells you the “message was not encrypted”
Hover showing "message not encrypted"
Using TLS removes the open red lock.
Mail sent over TLS
These messages went to spam because, well, do you know how hard it is to find a mail server that’s not authenticated? I ended up sending using SWAKS from one of our VMs so I could control a whole bunch of things, including whether or not mail used TLS. Interestingly enough, Gmail was happy to accept the mail over IPv6 but temp failed anything I sent over IPv4.
Gmail is, apparently, also notifying if mail being sent is going to a recipient on a server not using TLS. I don’t have an easy way to test that.

Q1 2016: Upcoming events
Thoughts on Data Hygiene

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Things you need to read: 2/5/16

gearheadAsk the Expert: How Can Email Marketers Stay Out of Gmail Jail and in the Inbox? The expert in question is an old friend of mine, Andrew Barrett. I met Andrew online in the late 90s, and we worked together (briefly) at MAPS. He was out of email for a while, but I’m pleased he came back to share his talents with us. The information in the article is valuable for anyone who struggles with getting to the Gmail inbox.
Unclutter Your Inbox, Archive & Keep Your Messages. Shiv Shankar talks about some new features at Yahoo Mail. With a simple click, you can archive email so it’s available to search, but not cluttering up your inbox. One of the things that jumped out at me from that article is that Yahoo is providing 1 TB of storage. That’s more than Google!
The EEC is doing a survey on the impact of CASL and want to hear from marketers. Go check out their blog post and take their survey.
Sparkpost has a guest blog from Alex Garcia-Tobar, co-founder of Valimail about common DKIM failures. I’ve met Alex a few times and I’ve always found him a pleasure to talk to. Alex is somewhat new in the email space, but he really gets some of the challenges in the authentication space. A lot of the issues he mentions in that blog post like lack of key rotation and shared keys are some of the technical debt I was talking about in my predictions for 2016 post.
What links have you read this week that are worth sharing?

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Filter complexity

URLBlockingForBlogDuring the Q&A last week, I mentioned an example of a type of filter trying to demonstrate how complex the filters are. There was some confusion about what I was saying, so I thought I’d write a blog post explaining this.

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July 2015: The Month in Email

Once again, we reviewed some of the ways brands are trying (or might try) to improve engagement with customers. LinkedIn, who frequently top lists of unwanted-but-legitimate email, announced that they’ll be sending less mail. Josh wrote about giving subscribers options for both the type and frequency of messages, and about setting expectations for new subscribers. In each case, it’s about respecting that customers really want to engage with brands in the email channel, but don’t want the permission they’ve granted to be abused. I also wrote a brief post following up on our June discussion on purchased lists, and as you’d predict, I continue to discourage companies from mailing to these recipients.

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