Microsoft using the List-Unsubscribe header

An interesting observation from Brian Curry about how Microsoft is using the List Unsubscribe header in their interface. The short version is that Microsoft is only supporting mailto: links. They’re ignoring any List-Unsubscribe links that are a URL.
Here are some screenshots.  When the sender is using a List-Unsubscribe <http://> header, Microsoft states that there is no information on how to help the user unsubscribe, so the offer to block the sender instead. Like in these two messages.
When the List-Unsubscribe header uses a mailto: link, Microsoft uses completely different language in the popup and does let the user know any future mail will go to the junk folder.

What does this mean?

We’re seeing a definite bias towards the mailto: link by various ISPs. Gmail has stated they prefer a mailto: link and Hotmail is refusing to support a http:// link. I think it’s good practice for every sender to use mailto: links. If this isn’t something software can handle, then that feature should be on the development roadmap.
There are a couple other things that I think are worth mentioning here.
First is that Microsoft is making it trivially easy to block senders that don’t use the List-Unsubscribe header (or just use the http:// version). Yet more evidence the ISPs are prioritizing user experience and making it easy for users to control what gets into their inbox. Blocking senders is not something that folks revisit very often. In those cases where I’ve put an explicit block in my mail client I may check it once ever couple years. Of course, the mail I block isn’t normally commercial mail, it’s people. But the principle is the same – it’s easy to block a sender and once individual blocks are set, they’re rarely reconsidered. This makes it even harder for senders to get to specific inboxes.
The second is that using the List-Unsubscribe header gets future mail from that address delivered to the junk folder. Again, a sign that user experience is one of Microsoft’s priorities. That means senders who are sending in the 10 day CAN-SPAM window aren’t actually reaching their recipients. That mail is going right to bulk.
The other issue is that Google revealed late last year that mail delivered to the spam folder at Gmail, even when that mail was delivered there by Google’s filter, negatively impacts the sender’s reputation. I, and I think other folks, were under the impression that continuing to send mail to the bulk folder was not going to actively hurt reputation. We were wrong. The reputation hit isn’t quite as big as when the individual user moves mail to the spam folder, but there is still a hit. If Microsoft is also looking at total mail to bulk then sending after an unsubscribe could hurt reputation overall.
Overall, use the mailto header for list-unsubscribes. Even if the “one click” unsub link ever get standardized, mailto is likely to be preferred by the ISPs.

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It depends… no more

The two most hated words in deliverability. Many people ask general questions about deliverability and most experts, including myself, answer, “It depends.”
There are a lot of problems with this answer. The biggest problem is that it’s led to the impression that there are no real answers about deliverability. That because we can’t answer hypothetical questions we are really just making the answers up.
Depositphotos_53649203_original
The reason we use “it depends” is because the minute details matter when it comes to deliverability. Wether or not something will hurt or help deliverability depends on the specific implementation. Who’s doing the sending? What is their authentication setup? What IP are they using? How were the addresses collected? What is their frequency? What MTA is used? Are they linking to outside sites? Are they linking to outside services? Where are images hosted? The relevant questions go on and on and on.
I am going to stop saying it depends when answering generic deliverability questions. Instead I will be using the phrase “details matter.” Details do matter. Details are everything. Details drive deliverability.
Details Matter
The importance of details is why many deliverability people hedge their answers. The details do matter.
I will do my best to stop answering It Depends to deliverability questions. Instead, I’ll be answering with question and pointing out the details matter.
 

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It's not fair

In the delivery space, stuff comes in cycles. We’re currently in a cycle where people are unhappy with spam filters. There are two reasons they’re unhappy: false positives and false negatives.
False positives are emails that the user doesn’t think is spam but goes into the bulk folder anyway.
Fales negatives are emails that the user does thing is spam but is delivered to the inbox.
I’ve sat on multiple calls over the course of my career, with clients and potential clients, where the question I cannot answer comes up. “Why do I still get spam?”
I have a lot of thoughts about this question and what it means for a discussion, how it should be answered and what the next steps are. But it’s important to understand that I, and most of my deliverability colleagues, hate this question. Yet we get it all the time. ISPs get it, too.
A big part of the answer is because spammers spend inordinate amounts of time and money trying to figure out how to break filters. In fact, back in 2006 the FTC fined a company almost a million dollars for using deceptive techniques to try and get into filters. One of the things this company did would be to have folks manually create emails to test filters. Once they found a piece of text that would get into the inbox, they’d spam until the filters caught up. Then, they’d start testing content again to see what would get past the filters. Repeat.
This wasn’t some fly by night company. They had beautiful offices in San Francisco with conference rooms overlooking Treasure Island. They were profitable. They were spammers. Of course, not long after the FTC fined them, they filed bankruptcy and disappeared.
Other spammers create and cultivate vast networks of IP addresses and domains to be used in snowshoeing operations. Still other spammers create criminal acts to hijack reputation of legitimate senders to make it to the inbox.
Why do you still get spam? That’s a bit like asking why people speed or run red lights. You still get spam because spammers invest a lot of money and time into sending you spam. They’re OK with only a small percentage of emails getting through filters, they’ll just make it up in volume.
Spam still exists because spammers still exist.
 

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Parasites hurt email marketing

As a small business owner I am a ripe target for many companies. They buy my address from some lead generation firm, or they scrape it off LinkedIn, and they send me a message that pretends to be personalized but isn’t really.
“I looked at your website… we have a list of email addresses to sell you.”
“We offer cold calling services… can I set up a call with you?”
“I have scheduled a meeting tomorrow so I can tell you about our product that will solve all your technical issues and is also a floor wax.”
None of these emails are anything more than spam. They’re fake personalized. There’s no permission. On a good day they’ll have an opt out link. On a normal day they might include an actual name.
These are messages coming to an email address I’ve spent years trying to protect from getting onto mailing lists. I don’t do fishbowls, I’m careful about who I give my card to, I never use it to sign up for anything. And, still, that has all been for naught.
I don’t really blame the senders, I mean I do, they’re the ones that bought my address and then invested in business automation software that sends me regular emails trying to get me to give them a phone number. Or a contact for “the right person at your business to talk to about this great offer that will change your business.”
The real blame lies with the people who pretend that B2B spam is somehow not spam. Who have pivoted their businesses from selling consumer lists to business lists because permission doesn’t matter when it comes to businesses. The real blame lies with companies who sell “marketing automation software” that plugs into their Google Apps account and hijacks their reputation to get to the inbox. The real blame lies with list cleansing companies who sell list buyers a cleansing service that only hides the evidence of spamming.
There are so many parasites in the email space. They take time, energy and resources from large and small businesses, offering them services that seem good, but really are worthless.
The biologically interesting thing about parasites, though, is that they do better if they don’t overwhelm the host system. They have to stay small. They have to stay hidden. They have to not cause too much harm, otherwise the host system will fight back.
Email fights back too. Parasites will find it harder and harder to get mail delivered in any volume as the host system adapts to them. Already if I look in my junk folder, my filters are correctly flagging these messages as spam. And my filters see a very small portion of mail. Filtering companies and the business email hosting systems have a much broader view and much better defenses.
These emails annoy me, but I know that they are a short term problem.  As more and more businesses move to hosted services, like Google Apps and Office365 the permission rules are going to apply to business addresses as well as consumer addresses. The parasites selling products and services to small business owners can’t overwhelm email. The defenses will step in first.
 

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