How to prevent outgoing email getting tagged as Spam

We’ve had a few questions raised recently about the issue of outgoing email being tagged as Spam. I thought it would be both fun and interesting to discuss the topic in this month’s blog post. I thought I might also touch on a few ideas to make your email less “Spammy”- looking.

A message tagged as Spam sent to a colleague or client is pretty irritating. In fact, the message probably won’t even get to its intended recipient with all the anti-Spam features available today. How do we resolve this problem? Well, no one method is full-proof. There will always be someone with what we call “super-paranoid restrictions” on their email. In these cases you’ll probably have to call the contact and get yourself added to their safe list of accepted email senders. For everyone else, here are some suggestions to get that email through.

Outgoing email being tagged as Spam:

If you determine that many of your clients are receiving your emails tagged as Spam the problem may reside in your email client’s configuration. If your email account resides on the Skyway West mail server the issue is easily remedied.

Our mail server handles email in two ways – SSL or non-SSL. SSL stands for Secure Socket Layer and its main purpose is to send your login information to the server securely. However, doing so also tells the server that you are allowed to send email from “here” (wherever “here” might be). If you are not using SSL on one of the appropriate ports our server authenticates you by your IP address. When you authenticate by IP the server forces your mail through our anti-Spam server since there is the chance that viruses could infect a machine and send out Spam from that machine. Authenticating with SSL says your user ID and password are valid and that is safe enough to bypass the Spam filter. Your mail is sent without further inspection by the system. Note: These settings are intended for users of Skyway West’s email server only. You should check with your provider to see if there are any similar options you have available on your mail server. For further instructions on setting up SSL if you’re on the Skyway mail server, click here.

What else can you do to make your email look less like Spam?

Many anti-Spam solutions work by assigning a threshold value which, if crossed, treats the email as if it was Spam. Certain characteristics about the email are assigned a value based on how “Spammy” that characteristic is. These characteristics and their values are then applied to the email, the values are totalled if they exceed the threshold value the server tags the mail as spam. Here are a few actions you can take to make your email look less Spammy.

Plain text: In the early days of email, plain text was the only option. Since then most (if not all) mail clients can do much more. You can style email with special fonts, add pictures, create links, etc. Unfortunately, these features can also make your email look like Spam. While it might look nice, when run through a Spam filter extra emphasis can be put on these HTML (HyperText Markup Language)- type emails. If it’s not absolutely necessary to make your email look pretty, Skyway West recommends using plain text messages to increase the odds your message will make it to its intended recipient.

Language. It has been said that a misspoken word can lead to tragedy. Unfortunately, a true statement in the Spam world. Spam filters look for keywords concerning pharmacology, sexuality and money schemes, among other subjects, and if they find them,  poof!… your message has been tagged. Even a simple sentence like, “Larry should go take a pill”, could trigger a Spam tag. In most cases this issue is of little concern, unless there are multiple instances of keyword tags (or unless perhaps you work at a pharmaceutical company!). Still, it is a good idea to really put some thought into your words before you click send. Some Spam engines include entire languages — Russian and other eastern european tongues, for example — in the accounting of demerit points that can push a given email over the spam threshold.

Redirection/Misdirection: Most people have probably subscribed to a newsletter email. These emails are really advertisements sent to you by a company or organization to let you know what’s new. Often they are filled with hyperlinks which will redirect you to a website to give you further details. Alas, these redirections can also add a value to a Spam score. The average user also often uses links in their everyday emails: in most cases the process is simply copying and pasting the URL into the email as its created. To keep your message’s Spam score down Skyway West recommends using link redirection sparingly.

For those of you interested in delving deeper into Spam scores and how they are calculated I’ll offer up this last URL (Uniform – or Universal – resource locator), which will take you to a site for a product called SpamAssassin that describes what kinds of traits are observed and how they are scored:

http://spamassassin.apache.org/tests_3_3_x.html

So there you have it. This will be my last blog entry on email for a while. What’s coming next month? You’ll just have to tune in to find out. Got a comment or question about any of my blog posts? Drop me a line at support@skywaywest.com or call into 604-482-1212. I might even answer your question in an upcoming blog entry. Always happy to hear from you. Until next month….

–Wes