TLS and Gmail delivery

I’m seeing some questions about TLS and Gmail. Folks are seeing a correlation between sending without TLS and the mail going to bulk.

Has anyone seen this? Are you sending mail with TLS and can’t get to the inbox? Or are you sending mail without TLS and getting to the inbox?

Inquiring minds and all that.

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Marking mail as spam says what?

I wear a number of hats and have a lot of different email addresses. I like to keep the different email addresses separate from each other, “don’t cross the streams” as it were.

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SNDS issues and new Gmail

A bunch of folks reported problems with Microsoft’s SNDS page earlier today. This afternoon, our friendly Microsoft rep told the mailop mailing list that it should be fixed. If you see problems again, you can report it to mailop or your ESP and the message will get shared to the folks who can fix it.
The other big thing that happened today was Gmail rolled out their new inbox layout.
It’s… nice. I’ll be honest, I am not a big gmail user and have never been a huge fan. I got my first account way-back-during-the-beta. I used it to handle some of my mailing list mail. I could never work out how to get it to stop breaking threads by deciding to put some mail into the junk folder. I just gave up and went back to my shell with procmail (now sieve) scripts. I still have a couple lists routed to my gmail account, and the filtering is much improved – I can at least tell it to never bulk folder certain email.
The feature I’m really interested in is the confidential, expiring email. I’m interested in how that’s going to work with non-Gmail accounts. Within Gmail makes perfect sense, but I don’t think Gmail can control mail once it’s off their system.

My best guess is that Gmail will end up sending some type of secure link to recipients using non-Gmail mail servers. The message itself will stay inside Google and recipients will only be able to view mail through the web. That’s how the vast majority of secure mail systems work.
If anyone has the secure message already, feel free to send me a secure message. I’ll report back as to how it works.

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August 2017: The month in email

Hello! Hope all are keeping safe through Harvey, Irma, Katia and the aftermath. I know many people that have been affected and are currently out of their homes. I am proud to see so many of my fellow deliverability folks are helping our displaced colleagues with resources, places to stay and money to replace damaged property.
Here’s a mid-month late wrapup of our August blog posts. Our favorite part of August? The total eclipse, which was absolutely amazing. Let me show you some pictures.





Ok, back to email.
We’re proud of the enormous milestone we marked this month: ten years of near-daily posts to our Word to the Wise blog. Thanks for all of your attention and feedback over the past decade!
In other industry news, I pointed to some interesting findings from the Litmus report on the State of Email Deliverability, which is always a terrific resource.
I also wrote about the evolution of filters at web-based email providers, and noted that Gmail’s different approach may well be because it entered the market later than other providers.
In spam, spoofing, and other abuse-related news, I posted about how easy it is for someone to spoof a sender’s identity, even without any technical hacks. This recent incident with several members of the US presidential administration should remind us all to be more careful with making sure we pay attention to where messages come from. How else can you tell that someone might not be wholly legitimate and above-board? I talked about some of what I look at when I get a call from a prospective customer as well as some of the delightful conversations I’ve had with spammers over the years.
In the security arena, Steve noted the ongoing shift to TLS and Google’s announcement that they will label text and email form fields on pages without TLS as “NOT SECURE”. What is TLS, you ask? Steve answers all your questions in a comprehensive post about Transport Layer Security and Certificate Authority Authorization records.
Also worth reading, and not just for the picture of Paddington Bear: Steve’s extremely detailed post about local-part semantics, the chunk of information before the at sign in an email address. How do you choose your email addresses (assuming they are not assigned to you at work or school…)? An email address is an identity, both culturally and for security purposes.
In subscription best practices — or the lack thereof — Steve talked about what happens when someone doesn’t quite complete a user registration. Should you send them a reminder to finish their registration? Of course! Should you keep sending those reminders for 16 months after they’ve stopped engaging with you? THE SURPRISING ANSWER! (Ok, you know us. It wasn’t that surprising.)

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