Sailing the Email Marketing Seas

We talk to a lot of people who have ended up on Email Blacklists and who are looking for help getting off of them. The two most common ways to get yourself blacklisted is to either get a workstation infected with malware or to try to do Email Marketing yourself.

For the purpose of this article, email marketing is any email that you are trying to send out to a large number of recipients for whatever reason. Newsletters, Mass Mail / Bulk Mail, automatic reminder notifications, they are all basically the same to a recipient mail server, and we get asked by many people running their own mail servers what they can do to avoid getting blacklisted.

This newsletter is broken down into three sections of information.

• Taking a Cruise – Covers the advantages of using a third party source for your email marketing.
• Row, Row, Row Your Boat – Tips and tricks to maximize your results when sending out bulk mail yourself from your own email server.
• The Bermuda Triangle – Highlights all of the horrible things that can happen if you choose to email from your server.

Email Marketing is Not Bad
Before we detail the problems you might run into, we want to state for the record that we are not against email marketing or harbor any opinion against organizations which make use of it as a tool to grow their business, communicate with their customers, or promote their products online. However after we discuss the pitfalls ahead, you might think again about hitting send on an email campaign from your server.

Taking a Cruise

When asked for quick advice from administrators on how they can safely send bulk mail, our short answer is almost always, “don’t try to send bulk mail yourself.” Because email is so important for day to day business communication, we strongly recommend using a specialized service designed for email marketing so that your business mail systems are not compromised.

Take the complications which usually arise when you try to do this yourself and combine them with the value added features that specialized services offer and it’s almost always cheaper in the end to have somebody else do the heavy lifting. Here are some examples of why this usually ends up being true.

Maintenance
Using a 3rd party mailing service can help streamline many of the processes that you would have had to do manually with your own mailing list. Typically these services will offer specialized tools for managing user lists and help by automatically unsubscribing users whose addresses bounce multiple pieces of mail.

Zero to Hero
Sudden surges in email flow raise lots of red flags to Email Service Providers (ESPs). If your server usually sends 100 emails per day but sends 10,000 in one hour, then all sorts of different countermeasures can be deployed to ward off spam. Dedicated mass email companies can deliver high volumes of email without triggering red flags because they always deliver high volumes of email.

Copy Cat
ESPs are no dummies. When they see identical messages they know they are bulk mail. When you send an identical message to more than one person in a short period of time, it can very likely be treated as junk. Dedicated services get around this is by having a strong reputation. ESPs learn to recognize professional bulk mailers and give them some leeway. They also usually space out deliveries over time as a courtesy.

Alice Doesn’t Live Here Anymore
Sending an email to a closed account or with a typo in it can be frustrating when you send one, but it is a sure sign of bulk mail when you send 10 close together. Email marketing services and software pay close attention to bounce back messages which signify closed accounts because ignoring these can have devastating effects at who will accept emails from you.

CAN-SPAM
Not only are you being a nuisance if you send mail that people don’t want, but you might be breakingthe law. Professional email marketers are usually very cautious to stay within regulations. Doing so is prudent not only for getting caught, but for getting your email accepted. Building CAN-SPAM compliance yourself takes time and energy.

If a tree falls in the woods…
What’s the point of sending out a bazillion messages if nobody gets them, or if they go to Junk, or if they never get opened? Which messages get good responses, which did not? When is the best time to send your mail? Did the version with the new images do better or worse than the one with the old ones? Get more out of your efforts by tracking where your messages are going and who is reading and who is clicking. Third parties compete with features like these and have dedicated teams working on getting the most out of each message for you. Take advantage of them.

Recommendations
There are many Email Marketing companies out there to choose from. We at MxToolBox have had experience working with and can recommend StreamSend, have worked with clients using Constant Contact, and we like MailChimp because it has a funny name. Additionally MxToolbox has recently partnered with Aweber and those folks over there will take good care of you.

Row, Row, Row Your Boat

If a 3rd party mailing service is not the right fit for your company, you can do it alone, but there are many things you’ll want to consider. While your mail server seems capable of sending lots of email, many people find out too late that lots of problems can arise when they try it.

Nobody likes Drinking from a Fire Hose
Don’t all of a sudden deliver thousands of identical messages to a server all at once. If you can trickle your messages out they will be much more warmly received.

Does Everyone want your Mailings?
This one may seem simple enough, but often times users sign up for Newsletter or Bulk Mailing without realizing it. To increase the inbox delivery rate of your messages, make sure that all recipients on your distribution lists actually want to receive the mail by providing good content that isn’t salesly or pushy and is intriguing to your audience. To help further confirm that individuals do want your mailings, we recommend using double Opt in. Obtaining permission to send your email is critical.

You Don’t Want ’em Slamming the Spam Button
When you send mass emails to people who never asked for them, they’re going to hit the spam button and this seriously adversely affects delivery. This action from the recipient will definitely get you in trouble with Email Service Providers, and could get your email and IP address blacklisted.

Don’t Hide the Unsubscribe Button
While using Opt in to confirm your recipients is highly recommended, you will also want to make sure it is easy for your users to Unsubscribe if they desire. If users can’t unsubscribe easily, they may just mark your message as spam and that hurts your reputation. We recommend making sure the Unsubscribe button is easy to spot and the process to unsubscribe is a painless as possible.

Complicated Technical Tomfoolery
There are many different means and systems out there that have been created to try to help senders verify themselves so they can be trusted by recipients. They can be very complicated and spell disaster if configured incorrectly. They each have different pros and cons and are each implemented using different techniques. Some of these tools are:

• Reverse DNS – A DNS record for the IP address that you send mail from points to your domain. You can read more about rDNS in our forums.
• SPF Record – We only recommend configuring this if you are extremely comfortable with your network. If this is not configured correctly it can negatively impact mail flow or cause bounced messages. We would recommend using the Open SPF Wizard to configure your SPF record.
• Domain Keys – “DomainKeys” creates a domain-level authentication framework for email by using public key technology and the DNS to prove the provenance and contents of an email.
• DKIM – DomainKeys Identified Mail (DKIM) lets an organization take responsibility for a message while it is in transit.

The Bermuda Triangle

Measures Taken Against Bulk Mailers
Administrators of email servers are free to take any actions that they choose best when trying to detect and defend against malicious attacks, spam, viruses, and bulk mail. They draw the lines of what they consider a threat and they dictate the penalties for crossing their lines with the sender having little to no recourse that they can take. Here are some of the things you can experience if you aren’t careful.

Being Blacklisted – It feels about as bad as it sounds. Your IP or domain name gets put on a list. These lists are independently operated and specialize in different fields such as Spam, Viruses, ect. Administrators can subscribe to these lists, usually for free, and then take whatever action they like. The modus operandi is to reject connections from IP addresses on a blacklist resulting in a major delivery issues for all of your mail.

Getting Graylisted – The receiving server lets you go through the trouble of transmitting your email just to return a 400 response, which means try again later, on purpose. This results in the email being delayed since your server will wait before it retries. It also means that you have to burn twice as much bandwidth and CPU to get it delivered and that’s if they only make you try 2 times.

Throttling – Usually traffic over the Internet goes as fast as the pipes being used will allow. There are complicated means of accomplishing this that go on in the background. However one side of the connection can easily set the speed limit to slow things down if they like. This can be done for resource conservation for a receiving server but could also be employed to force a  sender to use up more of a precious resource – time.

Tarpitting – Basically this just means that as your server is talking to their server, they just take a short little break between each communication. The result is that it slows down the rate of transmission. If your server is configured to only have a set number of connections open at once, it can also cause your queues to back up.

Blackhole – Hey nice email. Let me put that someplace nice…right over here in the bit bucket. Gone forever. No bounce, no nothing. Not very fun.

One Man’s Garbage – Is nobody’s treasure. Off your messages go to the junk folder to hang out with some of the worst messages ever dreamed up. Sometimes even messages that aren’t part of the campaign get junked because they come from a source of bulk mail.

Additional Resources
Moms Email Marketing Tips
Bulk Email Help

July Newsletter
A Castle in the Clouds – Google Apps