This is one of the greatest questions facing online marketers as we suffer through yet more years of spam and its impact on Web commerce. Some folks recommend that you just walk away from email and focus exclusively on RSS feeds and related channels, but I haven't changed my opinion that email really is the killer app of the Internet and I still love getting good, useful, interesting mail.

I also send out a fair amount of mail to lists ranging from a dozen to thousands of subscribers, and I know exactly what you mean about having one wrong word or one "suspicious phrase" causing major corporate gateways to either categorize your mail as spam, thence to be automatically filed in the recipients junk folder, or outright rejecting it without any human intervention. Or, worse, automatically reporting you to one of the mail blacklist services, causing even greater deliverability problems down the road.

One of the best ways to avoid these issues is to look into an email marketing company.

Email expert Anne Mitchell is one of my good friends and truly is an expert on spam and email deliverability. I asked her this very question and here's her advice:

"The most important thing of all is to listen to your common sense, and *not* the email marketing "experts". For example, sending HTML can wreak havoc with a mailing, and not all mailings really *need* HTML. But so many email marketing experts, in-house marketing departments, and email marketing consultants insist that you have to use HTML to get a decent open rate. Well, you won't get a decent open rate if nobody is receiving your email, and it may well be that your particular audience couldn't care less whether their email arrives as HTML, plain text, or semaphore! In fact, lots of people *prefer* plain text.

"It's also really important to familiarize yourself with how the most popular spam filters work, particularly spam filters such as Spam Assassin. Once you realize that they have a check list of "spammy" words and phrases that they are looking for, and that every time you use one of those words or phrases (which are listed in our book) in your email you are getting a demerit, and when you hit a certain number of demerits your email gets junked, you can start to effectively tweak your email to avoid those traps. Such seemingly positive words and phrases as "money back guarantee", "no obligation" and, yes, "click here to unsubscribe" can cause you problems.

"You also need to look at your own email sending infrastructure, because it can cause you problems no matter how sterling is the content of your email. Do you publish SPF? Do you have rDNS set up? Are you using only real email addresses which receive email as your "from address"?

"And that's only the tip of the iceberg. As you can see, there is a LOT to optimizing your email deliverability."

Finally, if this is a topic that's critical to your business, I highly recommend you check out Anne's The Email Deliverability Handbook: Getting Legitimate Email Delivered in a Spam-Filtered World. It's full of smart advice and suggestions from Anne and her clients, and will pay for itself (it's $99) when your email deliverability improves and more customers see - and act upon - your next newsletter, I'm sure. Or, even better, Anne has a package that includes the ebook, another ebook on how to be CAN-SPAM compliant, and her Child Protection Email Address Registry Law Seminar too. You can buy that $197 package here: Buy Anne's email deliverability package.