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Marketing - email delivery issues

You've worked hard to build your subscriber list. Your marketing team has created a great email campaign; the subject line and content irresistible. You have click tracking software in place to record results and a kick butt landing page. You've tested the email on a small group of people first and received great feedback.

But there's few sales. Click rates aren't what you expected. Even more confusing, email open rates are incredibly low.

What could be wrong?

Welcome to the frustrating world of email delivery problems. It's possible that your subscribers aren't even seeing your marketing message.

I have a love/hate relationship with email filters. Without them it would be impossible for me to work - I'd just be inundated with spam. On the flip side; with an increasing number of ISP's and web hosts using email filtering systems, it means that every word in my email marketing efforts has to be carefully considered as it could trip a filter and increase the spam scoring. It doesn't matter whether the people on my lists are double opt-in; filtering software just doesn't care.

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Email filtering aspects and delivery strategies

Email filters are becoming increasingly sophisticated; but they are far from perfect. The days of filtering software just checking content for obvious things are long gone; a battery of tests are used. 

It's important to note that in most cases, any single instance of the following points may not cause your email to not be delivered. Most filters assign a score to each element that fails a test; it's only once the score threshold has been exceeded that the email is blocked.

When approaching the issue of deliverability, don't take the mindset of beating spam filters, approach it as working with them. Beating spam filters is what spammers do ;).

Header filters

Email headers, the information that's not viewable when you open an email, contain information showing the point of origin of an email. A header filter examines this information to see if these details are forged. While this doesn't pose a problem for most legitimate marketers; it can be an issue if you are using a dubious list service to deliver your campaign. There's also other items in the header that indicate your communication is generated by list software. Again, this won't necessarily prevent your email being delivered, but it does draw attention to it.

Other issues such as not using a name in the "from" field, only an email address, can add to your score. Even innocent mistakes like having your computer clock set too far forward can attract attention.

Sending email via your ISP, but specifying a different email address in the "Reply to" field can also be a problem, as can sending to too multiple recipients via cc and bcc. It's always best to use specialized mailing list software for lists containing more than a dozen names.

For more information regarding header filters, take a look at SpamAssassin's list of tests.

If you're interested in seeing what is actually in an email header and aren't sure how to view it

Open a message, go to "View" and click "Options". The header will be displayed.

Outlook Express:
Highlight a message, select "Properties" from the File menu. Then click the "Details" tab, followed by "Message source". 

Open the email and on the menu bar click View, select Headers and choose "All".

Permission filters

Permission filters, are quite straightforward; they just block all email attempting to be delivered to a mailbox that doesn't originate from an authorized source. Most permission filters will send a challenge to the sender, giving them instructions on how to continue with email delivery. Permission filters are usually controlled at a user level. If you have a hundred people on your list using permission filters, it can be a huge time waster in getting your email address whitelisted.

To minimize the impact of this, when a visitor subscribes, flag with them on the successful submission/confirmation page that they should ensure that your email address is in their address book or whitelisted with whatever service they are using.

Content filters

This is where things start getting really challenging. A couple of years ago, I could have published up a list of "poison" words that will prevent delivery, but the list is just getting too long. Remember that "poison" words only become so in most cases when the ratio is too high. For example, in some scenarios, the word "free" just can't be avoided, it's an important part of your campaign. Some marketers try to get around this by using words like "fr*e". It's my opinion that this is not a good strategy because:

a) It looks tacky - won't impress your subscribers
b) I'm sure that most filters are aware of this variation :)

All things in balance. If you use those kinds of words, ensure there's other text to offset any score that may be applied. This is one of the strategies that spammers use - they'll hawk their wares at the top of the email and you'll see a couple of paragraphs that may be just an excerpt of a book below it. I'm not recommending that you do that at all, in fact I strongly advise against it. The accompanying text must be totally relevant to the campaign.

Again, SpamAssassin's list of tests is a good resource for reviewing poison words. Some other general guidelines:

  • Do not "shout" in your email campaigns by using caps lock

  • Avoid using multiple exclamation marks

  • Don't use exclamation or question marks in the header

  • Do not embed scripts in your email

  • Use valid HTML 

  • Use a proper title tag - not the default used by your web page editor

  • Don't use light colored fonts on a light background or dark font color on a dark background.

  • Definitely do not state "this is not spam". It's a line that spammers use.

  • Use terms like "free", "limited offer", "bonus", "buy now" and related terms sparingly.

  • In relation to the above; don't try strategies like F R E E or F*ree to get around the filters, they can detect obfuscation

  • Using an image to display poison word text may work, but bear in mind that an email containing only images will also throw up a red flag.

  • Don't add in a stack of blank lines

  • Don't have an @something-offers from address

  • Try not to use the word "buy" in subject lines

  • Don't use large fonts

  • The use of "dear" or "dear friend" in a subject line while increase your spam score

  • The word "guarantee" should be used sparingly

  • Image only emails are more likely to trigger a score

The best way to ensure your email will pass a filter test is to run your email through a testing application first. The better mailing list management services offer this kind of feature. The test results will not only provide you with a pass/fail report, but also details of where your email failed.

Alternatively, if your host/ISP is using spam filtering, it should be indicated in the header; perhaps along with a spam score and what elements triggered that score - for example: 

X-Spam-Checker-Version: SpamAssassin 3.2.x on example.com
X-Spam-Status: Yes, score=8.4 required=5.0 tests=BANG_GUAR,HELO_DYNAMIC_HCC,

You can try sending your the promo blurb you wish to send from an address external to your ISP/domain to your ISP/domain; see if it gets through, what score it achieved and what triggered scoring.

Blacklisted mail IP

In a shared hosting situation, it's quite possible that another user using the same mail server could be spamming, which then gets the entire mailserver blacklisted. Even if you have your own IP, you may be inadvertently blocked by an ISP for any number of reasons; so monitoring during a mailout is crucial.

A quick check you can run is to enter your outgoing mail IP into SpamHaus's Block List and  SpamCop's Block List before sending out your campaign, during and after. If you should find the mailserver listed, contact your ISP/host. If you find that the mailserver you are sending from is blacklisted; don't attempt to remove the blacklisting yourself. If there is a spammer using that server and it gets reported again, the blacklisting will remain in place for longer - the spammer must be dealt with first.

It's also very important that you monitor bounces and act on any spam complaints. Ignoring a single serious spam complaint is enough to get you blacklisted or if your host is particularly touchy; to have your account suspended. A bounced email will usually contain the reason why it bounced.

Another very frustrating issue are false spam reports. For example, AOL users are well known for reporting a legitimate newsletter as spam instead of just simply unsubscribing - it's very frustrating. AOL will generate an automated spam complaint; it's wise not to ignore it as if there are many generated, you may find all your emails to that service blocked. Simply remove the user from your list.

Always ensure that your unsubscribe process is simple and clear - don't give subscribers an excuse to file a report. Using a double opt-in process for subscriptions will also reduce the risk of reports.

email marketing tips, software and reviews

Autoresponder software 
& mailing list managers

Get more from your email
marketing - tips, reviews 
& free trial software/services.

High mail traffic

Another aspect that can throw up a red flag to ISPs is the volume of mail hitting their services from a single source. If you have a large list, it's recommended that you don't send out in order of ISP. Deliver the email in alphabetical or date subscribed order as this will reduce the amount of email going to any particular ISP in a short space of time. 

It's also not unheard of where the volume of all incoming mail to an ISP is at such a level that they simply start bouncing messages instead of delivering. The best way around this is to send your campaign on low traffic days, usually Sunday or early Monday morning.

Further delivery strategies

One of the easiest ways to determine if your mail is getting through to your subscribers is to open an email account with major services such as AOL, Yahoo and Hotmail. If your email isn't being delivered or winding up in the bulk folder of just one of them; you should contact that company for advice. You may not have to go to the trouble of opening email accounts if you're using a list management service, check the features to see if delivery reports are available.

Some of the larger ISP's have whitelist programs that you can apply to, such as AOL's bulk sender status. If you're working with a reputable list management service, the company may already have this status with many providers.

Many ISP's and hosts also give a degree of control to their users by providing a whitelisting function whereby the user can specify that emails coming from X address do not need to be filtered.

Having a great marketing message is only one aspect of successful email marketing - delivering it is most definitely one of the biggest challenges facing all of us in ecommerce today. Every subscriber who misses out on receiving your communications directly translates to effort wasted, increased labor costs and reduced profits.

Further learning resources

List management software and services - review

Gauging email open rates

Click tracking - software and tips

Creating effective landing pages

Michael Bloch
Taming the Beast
Tutorials, web content, tools and software.
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Copyright information.... This article is not available for reproduction without express written permission from Michael Bloch. 

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