Brent Hodgson, Copywriter

Copywriter and Internet Marketing Consultant

E-mail Deliverability hacks - the Truth

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Email Deliverability and spam filtersDeliverability is a big issue when you’re marketing via a newsletter, ezine or autoresponder series.

But one thing I HATE WITH A PASSION is seeing this:

FR’EE

An apostrophe?… What the heck!

Jim Edwards uses it, so does Jacon Stein, Glenn Dietzel, Vincent Rich, Scott Bywater, Glen Hopkins, Tom Hua, Ted Ciuba - the list goes on…

It’s completely unnecessary from a Deliverability / Spam Filtering perspective, and it can LOWER your conversion rates.

Seeing the word “free” broken up by apostrophes, full stops and asterisks is a clear indication to a spam filter that the e-mail IS SPAM!

Internet Marketing Myth #47: The word “free” sets off spam filters.

In most cases, it does not.

Otherwise, a whole heap of legitimate e-mails would trigger false positives.

ie:

…Are you free for dinner on Friday night?…

or;

…Here’s that report for review. Feel free to make changes as you see fit…

On the other hand, using apostrophes and other characters to break up words CAN hurt your Deliverability and Conversion Rates.

Spam filters are getting smarter. Some (such as Bayesian spam filters) even learn to recognise patterns in spam, so they become more accurate over time.

A clear tip-off that an e-mail may contain spam is using apostrophes (or other characters) to break up words.

But what’s worse is the effect it has on the person reading your message.

The moment they see words broken up by unnecessary apostrophes, the reader instantly recognises that this is another sales pitch, and subconsciously associates you with the dozen or so spammy junk e-mails they just deleted.

“Delete!”

However, there is some truth to this Deliverability myth

In certain contexts, the word “free” does trigger red flags (and can potentially cause deliverability problems) with some spam filters.

I’ll use SpamAssassin as an example.

SpamAssassin is open-source anti-spam software, and is one of the most popular and widely used spam filtering tools available today.

When it comes to using “free” in marketing e-mails, there are several ways you can trigger a red flag and affect deliverability - including:

  • Placing the word “free” in capitals in the subject of the e-mail;
  • Starting the subject with the word “free”;
  • Using the words “Risk Free” or “Financial Freedom”;
  • Offering a free quote;
  • etc..

But by themselves, none of these trigger a red flag strong enough to cause deliverability issues with SpamAssassin users.

Most of the examples listed above will give a spam score of +1… which is well short of the 5 points necessary for an e-mail to be marked as spam.

In fact, some of the biggest “red flags” SpamAssassin uses to detect spam are to do with text disguised within an e-mail.

These include:

  • Disguising text in your message using unknown or foreign character sets, HTML obfuscation or base64 encoding (up to +3.6 spam points);
  • Disguising words by mixing upper case and lower case letters together inside a word (+3.5 spam points);
  • And having certain words disguised using apostrophes and other characters.

Using tracking ID’s inside your e-mails can also hurt deliverability (+2 spam points).

And always avoid the deadly sins of faking e-mail headers and mentioning drugs or prescriptions (+ heaps!)

Final words on E-mail Deliverability

Don’t use ridiculous tactics to try and get around spam filters, just because you saw another internet marketer using them.

Anti-spam experts know the best way to improve their systems is to look for the tricks spammers are using, and squash them.

The best steps you can take when it comes to your e-mails are:

  1. Write your e-mails as if you were writing an e-mail to your best friend, and you wanted them to click on the link in your e-mail to take advantage of your offer.
  2. Write for your readers, and concentrate on creating a strong sales message. Don’t write for spam filters!
  3. Send your e-mail broadcasts with a popular mass e-mail tool, not some cheap alternative which might fake header info and cause you deliverability problems.
  4. And, after all that, if you’re worried about deliverability, test your e-mail by running it through a few different spam filters. That should give you an idea about your expected rate of E-mail Deliverability.

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Posted to Categories: Copywriting · Internet Marketing Strategy

February 11th, 2007 · Brent Hodgson

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7 responses so far ↓

  • 1 Casey Woods // Feb 11, 2007 at 3:08 pm

    You’re dead on with your comments. You need to send a pretty obnoxious email before it gets flagged purely based on Bayesian analysis. If the email is well written and doesn’t do stupid stuff like capitals or intentional misspellings then you should be fine.

    In my experience, most delivery issue result from crap email software, messed up headers, bad HTML, being on an RBL list, having misconfigured DNS, not having SPF records in place, etc.

  • 2 Shaun // Feb 11, 2007 at 6:04 pm

    Hi Brent,

    Good Post!

    My question to you is that given this post what do you believe is the normal deliverability rate that email marketers get? We hear that deliverability in Australia is slow and I for one am a big believer of this. Also while on this point have you noticed lately that the spam testing software on spamarrest and other sites are not returning true results?

    In your experience Brent are their certain thinks that a marketer should do to get through spam firewalls.

    Personally we have been doing some testing with some of our clients and have been able to increase our deliverability by over 400%. This is a big figure when you look at the impact on sales this has.

    Your Thoughts?

    Shaun

  • 3 Brent Hodgson // Feb 12, 2007 at 2:20 am

    @ Casey - Thanks for your comments. You’re right problems with DNS records, bad HTML, and bad headers are some of the big “red flags” that set off spam filters - not content.

    @ Shaun - Deliverability and open rates are difficult to track. Especially if you’re sending text-only e-mails (like most of mine are).

    Tools like Delivery Monitor (http://www.deliverymonitor.com/) get around this by having a bank of e-mail addresses which go through various ISPs, e-mail providers and spam filtering software. They then watch to see whether e-mail broadcasts make it into the inboxes, spam folders, or just don’t arrive at all.

    I use a similar tactic when I’m running a broadcast. I’ll send a test broadcast to a series of Hotmail, Yahoo, Gmail, and ISP e-mail addresses which are running a variety of spam filters (SpamAssassin, Barracuda, SpamBayes, Mailwasher Pro etc).

    If my e-mail is delivered to all of these e-mail addresses, I can be confident that my deliverability rates will be as close to 100% as possible.

    As you say, this makes a big difference to sales.

    Here’s an example…

    In the past, I’ve found that up to 30% of people use Hotmail addresses when they’re signing up to web-sites and filling in squeeze pages. So if e-mails aren’t getting through Hotmail’s spam filters, then you could be flushing up to 1/3rd of your sales down the drain!

    That’s crazy!

    But a 400% improvement - sheesh! That means their delivery rates were under 25%! I’ve never heard of someone’s deliverability rate being THIS low.

    As for SpamArrest - I don’t use this. But I do use Barracuda at the office, and we’re constantly dealing with false positives.

    The two causes I suspect are:

    1. When I receive “too many” similar e-mails from the one e-mail address, Barracuda marks them as spam (which is why you should look at throttling down send rates when you’re doing broadcasts), and;
    2. Because of legitimate marketers trying to use “spam avoidance” hacks, like the ones I mentioned in my post.

    Really, I don’t use any tricks - I just write naturally, and then test.

    There are more questions in your comment, but already there’s a heap of info here. So I think they’ll have to wait for another post ;)

  • 4 Brent Hodgson // Feb 12, 2007 at 2:30 am

    @ Shaun - Just on SpamArrest.. It just struck me what you’re talking about.

    There are three reasons why you should always monitor the e-mail address which sends your e-mail broadcasts.

    1) So that you can monitor e-mail addresses which are bouncing, and remove them from your database (which has several positive effects on your database - which I might address in a later post);
    2) Because people occasionally reply with the words “Unsubscribe” in the subject line (instead of clicking an unsubscribe link) and in Australia it can cause some problems if you don’t unsubscribe someone within 5 business days.
    3) So that you can look for whitelist validation e-mails (such as SpamArrest’s validation e-mails) and ensure that subscribers using annoying anti-spam whitelists still get your e-mails;

    Man! There’s enough here for another post!

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