Beating the SPAM filters.
I was noticing that all of my email announcements were always getting sent to the SPAM/Bulk box in my Yahoo! email account. Now, Yahoo! is, in my opinion, way too SPAM-filter-happy, but that got me wondering: if Yahoo! is sending my emails to the SPAM box, how many other email services might be doing the same?
That got me worried, especially since I had reason to believe that a fair percentage of people weren't getting my support emails. That's one of the reasons I switched to my support-ticket system instead of doing straight email support.
So I decided to do some testing and research and figure out why Yahoo! was filtering my emails into the SPAM box. Hopefully what I discovered will help you if you find yourself in a similar situation. Also, since Yahoo! is so SPAM-filter-happy, it made sense that if I could figure out how to get past their filters, it would get past almost everybody else's, too.
(Just an aside: GMail has never flagged any of my emails as SPAM. Yahoo! is the only mail provider I've used who would consistently flag my messages as SPAM.)
The first thing I did was look at the full headers of the messages that were going into the SPAM folder. I noticed that it had this line in it:
That told me that Yahoo! considered my message to be part of a bulk mailing--which, in fact, it was, though that alone isn't enough reason to put it in the SPAM folder. So I knew there must be something else going on.
Step by step I tried everything. I changed the FROM field of the message so that it appeared to come from a different domain. I also changed the TITLE field to the title of a message that did not get sent to the SPAM folder. Neither of those actions caused any change--the message was still landing in the SPAM folder.
So I took out the BODY completely and changed it to the BODY of a message that didn't get sent to the SPAM folder. Lo' and behold, the message made it directly into the inbox!
So I started dissecting the BODY to figure out which part of the body was causing the message to land in the SPAM folder. After a few tests, I realized that it was my domain name (jonathanleger.com) appearing in the BODY that was causing the problem.
Then it all made sense. You see, Yahoo! (and other ISP's) give people the ability to click a button that labels the message as SPAM. Now, some people "forget" that they opted-in, but others simply don't realize that by flagging a message as SPAM, they are causing problems for the owner of the list they are on. If you have an opt-in list, you know what I mean--so called "SPAM reports" coming from people who have opted-in of their own accord. It's frustrating, but it's a fact of life in the list-building world.
Yahoo! had gotten the wrong impression about my jonathanleger.com domain, and that domain name just appearing in the BODY was causing Yahoo! to flag my message as SPAM.
The solution? I simply used a new domain (jonleger.com) to redirect people to the pages of jonathanleger.com. When I include jonleger.com in the BODY, Yahoo! lets the messages into the inbox with no complaints.
So if you find yourself caught in the SPAM filters, run a few tests to see if perhaps a domain name you're putting in the BODY has been misflagged as a source of SPAM. If so, use a redirect work-around like I did to get past it.
Here's a tip that got posted in the comments for this post. The tip was so good I had to include it here:
(That tip was submitted by Roger Seher.)
I'm not alone in the struggle against the SPAM filters, as some of the top Internet Marketers in the world are landing in my SPAM folder these days (including the likes of Mike Filsaime). Maybe they'll read this post and implement the work-around themselves. 
