Is your mail being bulk foldered?

Daisy at Signup.to posted a list of 11 things to do when mail is going to the bulk folder. Her suggestions are a good start to troubleshooting and fixing persistent bulk foldering of mail.
One thing she doesn’t mention is that while bulk foldering can sometimes be the result of poor content, more often it’s the result of unengaged recipients. Think of bulk foldering this way: the ISP has some subscribers they’re pretty sure want your mail, so they’re not going to block your mail. But they’re pretty sure a lot of subscribers don’t want your mail so they’re not going to deliver it to the inbox.
The trick to getting mail moved out of the bulk folder is to get more people engaged with your email marketing. This is tough to do if they’re not actively checking their bulk folder for mail but there are some ways I’ve helped clients get mail into the inbox.

  1. Contact customers through a method other than email. This works well to remind them to look for your mail. You can also tell them how to add your From: address to their address book which will override the ISP bulk foldering decision.
  2. Segment your list and focus on engaged subscribers. Improving the reputation of your IP addresses and content will help improve delivery. Focus on those people who are highly engaged (clicks and opens) and stop mailing those people who aren’t reading your mail any way.
  3. Create a re-engagement campaign with enticing subject lines. Your goal is to get unengaged recipients to actively seek out your email in their bulk folder and move it to the inbox. Having good subject lines (test, test, test) is critical to this effort. People just glance through their spamfolder and don’t open mail unless the subject line catches their interest. If you can catch their interest enough to have them open the mail and move it to their inbox then you’ll end up in their inbox by default.
  4. Let go of your unengaged recipients. I know it’s difficult to admit that it’s over between you and some of your recipients. But, it really is over. The longer you hold on to them the more they’re going to hinder your relationship with other recipients. Dropping the long term unengaged off your list will help increase your reputation and inbox delivery.

None of these are quick fixes. When I’ve worked with clients to deal with long term bulk foldering problems it’s taken from 2 to 4 months to resolve the issue. In some cases it did require contacting the ISP to get them to recalculate the reputation, in other cases the ISPs changed their filtering without any contact needed.

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Content based filters

Content based filters are incredibly complex and entire books could be written about how they work and what they look at. Of course, by the time the book was written it would be entirely obsolete. Because of their complexity, though, I am always looking for new ways to explain them to folks.
Content based filters look at a whole range of things, from the actual text in the message, to the domains, to the IP addresses those domains and URLs point to. They look at the hidden structure of an email. They look at what’s in the body of the message and what’s in the headers. There isn’t a single bit of a message that content filters ignore.
Clients usually ask me what words they should change to avoid the filters. But this isn’t the right question to ask. Usually it’s not a word that causes the problem. Let me give you a few examples of what I mean.
James H. has an example over on the Cloudmark blog of how a single missing space in an email caused delivery problems for a large company. That missing space changed a domain name in the message sufficiently to be caught by a number of filters. This is one type of content filter, that focuses on what the message is advertising or who the beneficiary of the message is. Some of my better clients get caught by these types of filters occasionally. A website they’re linking to or a domain name they’re using in the text of the message has a bad reputation. The mail gets bulked or blocked because of that domain in the message.
One of my clients went from 100% inbox every day to random failures at different domains. Their overall inbox was still in the 96 – 98% range, but there was a definite change. The actual content of their mail hadn’t changed, but we kept looking for underlying causes. At one point we were on the phone and they mentioned their new content management system. Sure enough, the content management company had a poor reputation and the delivery problems started exactly when they started using the content management. The tricky part of this was that the actual domains and URLs in the messages never changed, they were still clickthrough.clientdomain.example.com. But those URLs now pointed to an IP address that a lot of spammers were abusing. So there were delivery problems. We made some changes to their setup and the delivery problems went away.
The third example is one from quite a long time ago, but illustrates a key point. A client was testing email sends through a new ESP. They were sending one-line mail through the ESPs platform to their own email account. Their corporate spamfilter was blocking the mail. After much investigation and a bit of string pulling, I finally got to talk to an engineer at the spamfiltering company. He told me that they were blocking the mail because it “looked like spam.” When pressed, he told me they blocked anything that had a single line of text and an unsubscribe link. Once the client added a second line of text, the filtering issue went away.
These are just some of the examples of how complex content based filters are. Content is almost a misnomer for them, as they look at so many other things including layout, URLs, domains and links.

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Why do ISPs do that?

One of the most common things I hear is “but why does the ISP do it that way?” The generic answer for that question is: because it works for them and meets their needs. Anyone designing a mail system has to implement some sort of spam filtering and will have to accept the potential for lost mail. Even the those recipients who runs no software filtering may lose mail. Their spamfilter is the delete key and sometimes they’ll delete a real mail.
Every mailserver admin, whether managing a MTA for a corporation, an ISP or themselves inevitably looks at the question of false positives and false negatives. Some are more sensitive to false negatives and would rather block real mail than have to wade through a mailbox full of spam. Others are more sensitive to false positives and would rather deal with unfiltered spam than risk losing mail.
At the ISPs, many of these decisions aren’t made by one person, but the decisions are driven by the business philosophy, requirements and technology. The different consumer ISPs have different philosophies and these show in their spamfiltering.
Gmail, for instance, has a lot of faith in their ability to sort, classify and rank text. This is, after all, what Google does. Therefore, they accept most of the email delivered to Gmail users and then sort after the fact. This fits their technology, their available resources and their business philosophy. They leave as much filtering at the enduser level as they can.
Yahoo, on the other hand, chooses to filter mail at the MTA. While their spamfoldering algorithms are good, they don’t want to waste CPU and filtering effort on mail that they think may be spam. So, they choose to block heavily at the edge, going so far as to rate limit senders that they don’t know about the mail. Endusers are protected from malicious mail and senders have the ability to retry mail until it is accepted.
The same types of entries could be written about Hotmail or AOL. They could even be written about the various spam filter vendors and blocklists. Every company has their own way of doing things and their way reflects their underlying business philosophy.

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I'm on a blocklist! HELP!

Recently, an abuse desk rep asked what to do when customers were complaining about being assigned an IP address located on a blocklist. Because not every blocklist actually affects mail delivery it’s helpful to identify if the listing is causing a problem before diving in and trying to resolve the issue.

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