Everybody remembers that old Johnny Cash song Folsom Prison Blues. What very few people know is there was actually an omitted verse:

“I sent some spam in Reno,

just to win some clicks.

I left out an unsubscribe link

and bought an email list”

Okay I completely made that up, but still email marketing is one of the more tightly regulated aspects of internet marketing. While building bad links could hurt you with a manual penalty from search engines (we wrote about how bad links can hurt you here), sending out emails that don’t comply with federal regulations can leave you with a massive fine or worse.


Perhaps the most ironically named piece of legislation in US History, the CAN-SPAM Act (short for Controlling the Assault of Non-Solicited Pornography And Marketing) outlines regulations for sending out “commercial electronic mail messages.”

To clear up any confusion/prevent sneaky misinterpretations, the law defines a “commercial electronic mail message” as “any electronic mail message, the primary purpose of which is the commercial advertisement or promotion of a commercial product or service…”

“But wait!” You eagerly interject. “I’m just trying to promote my content.” self-impressed by the legal loophole you believe you’ve found.

The law addresses content marketing promotion by including “content on an internet website operated for a commercial purpose” in its list of applicability.

Basically, any email whose goal is driving traffic or converting leads for a commercial website needs to follow the law.

You may not need to worry about any of this

Thanks for reading so far, but you may not have had to read any of this. If your email marketing is done through a service like Mad Mimi, Mailchimp or Constant Contact, the following tips will be useful only as knowledge to be passed down to your own padawans.

Email marketing services cover their digital butts by requiring clients to provide the information, and abide by the protocols outlined in the CAN-SPAM Act. They often will warn you if you have customized a field in a manner that’s not in accordance with the specifics of the law.

But I’m too pretty to go to jail!

Follow these tips, and you wont need to worry about shaving your head or selling cigarettes in the cafeteria.

Read them, memorize them, laminate them, incorporate them into your wedding vows.

If you have any hand in email marketing for a small or medium size business, they could keep you out of the old Crowbar Hotel.

1. Don’t forget the unsubscribe button

Every email you send out for commercial purposes needs to have a link or button that allows recipients to unsubscribe to your list.

Small business email marketing unsubscribe

Small business email marketing unsubscribe option

Unsubscribe Small Print Priceline

Notice something? Yeah they’re all very tiny and frustratingly hard to find. There is no requirement as to the size of the button/link, it just has to be present.

Additionally, any unsubscribe request must be handled within 10 days. From that point on, all sending to that email must cease and the only legal way to keep the address on record is for compliance.

2. Your physical address must be present

Anything else sticking out on all of these email footers? They all have the physical address of the commercial entity sending smack dab in the footer of the email.

If you’re a super villain in a secret underground lair, and I’ve just lost you, take heart – a PO Box can be used as well!

(Although, good super villains don’t worry about spam laws just sayin’)

Darth Vader at Long Beach Expo

“Grand Moff Tarkin – Fire up the planet destroyer and also send out a properly-formatted email letting the Empire know it will be on Youtube later.” Image credit to Wikimedia Commons

3. Represent yourself accurately

You know those letters that come in the mail with stenciled letters on the envelope that warn you of their urgent contents “URGENT ATTENTION NEEDED?” or “IMMEDIATE REPLY REQUIRED?” So you jump into Oh-my-gosh-what-is-it-was-my-credit-card-info-stolen-or-am-I-getting-sued-by-a-furniture-store mode and rip open the envelope only to see.


It’s amazing getting somebody to transition from panic to relief to blinding rage, but the direct mail people have cracked that code hard and use it as their go-to.

The CAN-SPAM Act prohibits these slimy tactics in email and requires you to represent yourself accurately in your commercial electronic mail messages. This means:

  1. “Subject” line must be relevant to email content – You’re not getting away sending an email with the subject “Account statement” and then an advertisement for a card with better points.
  2. “From” line must be accurate and represent the commercial source of the email – I couldn’t send an email with “President Obama” in the from line advertising my fourth of July sale on eyewear.
  3. A message cannot contain a false header – You know that little blurb that shows up next to the subject in an email client’s (think Outlook, Gmail, etc) preview mode? That also can not misrepresent the intent of the email.

Additionally, if you have won an email address from an individual without that individual explicitly signing up for sales or promotional emails, you must say “This is a marketing email,” or “This is a sales email.” in the body of the email.

Examples of how you could have gotten these email addresses

  • Lead signed up for information on separate product
  • Lead downloaded eBook from your site and used email address to get content
  • Lead purchased from your site or brick-and-mortar store in the past and you had his or her email address from that transaction
  • Lead’s email was passed on to you by colleague/connection

It is not illegal to send to individuals who have not opted in, but you must state why they are receiving sales or promotional communication and honor any request to be taken off your list within 10 days of him or her submitting it.

Which leads us to our final tip…

4. Purchasing email lists is stupid and illegal

Harvested email lists are lists compiled by the worst people (or software built by the worst people) alive. These people comb through email addresses that have been publicly posted on forums/news sites and other sources and group them by interest to market to a specific demographic.

Illegal Mailing List

As you can see, a quick Google search turns up a solid relevant first page of results. I’ve blurred the names of these companies, because they’re not technically doing anything illegal. Just like the really fun fireworks, it’s not illegal to sell these lists just to use them.

These lists contain two sources of danger that clue authorities into their status as an unearned, harvested list.

1. Hard bounces

Hard bounces are what happens when you try and send an email to an address that is no longer active/accepting mail. Professional email clients (like Mad Mimi or Mailchimp) will automatically remove hard bounces from your list. If the hard bounce rate is high enough, though, they will often ask you to delete the list in accordance with CAN-SPAM regulations.

2. Honeypots

Honeypots in general are snippets of code put into websites and other online communication that recognize attempted attacks to the website infrastructure or compromises to security.

In email marketing, they are also known as spamtraps or spamtrackers. They work a little bit differently.

Story time!

It’s the year 1999 and you’ve just signed up for your first Yahoo.com email account. The homepage looks like this

Yahoo in 1999

If you had Yahoo Pager, you were really ready to go

It’s already summer and you’ve gone all out on Millennium Fever, so you decide your email address is going to be [email protected] you sign up for your email and use it to get showtimes for Gladiator, and X-Men. Once 2001 hits, though, the email address feels dated.

By 2005, you’ve already moved on to  [email protected], and the email address has been lost to history. You find it on an old business card, though, and to protect your own privacy, finally go in and deactivate the email address…in 2009.

Now, once you deactivate your email address, Yahoo holds your it for one year. They perform minor analytics to see if any traffic is going that way and determine if any new users will claim the address. Since the address proudly featured the year 2000, it remains unclaimed

The day their 12 month period passes, they give [email protected] to an organization called Spamhaus. Spamhaus registers this email in their system as a honeypot, meaning that if anybody sends a message to this email address, they are alerted. When you signed up and subsequently closed that email address, you didn’t know it, but you were helping make the internet a less spammy place.

Go you, Web Fan!

Additionally, Spamhaus and similar organization SORBs buy unpopular web domains and build 1000s of email addresses on these domains which are designated from their birth as honeypots.

Purchased email lists are notorious for being riddled with honeypots. More than a few of them getting the same email, and your information is likely to be forwarded to the appropriate authorities for prosecution of violating CAN-SPAM.

Man getting arrested

Sadly, “They had to know about my discounted shoes, your honor. THEY ALL HAD TO KNOW!!” is not an admissible defense in court. Imaged credit to steven damron


The criminal side of CAN-SPAM violation has seen individuals incarcerated. The list of those who have felt the long arm of the law for violating the regulations is longer than any spam-inclined email marketer should be comfortable with.

Civil CAN-SPAM complaints handled by the Federal Trade Commission have seen defendants awarded as much as $900,000, as well.

These penalties may seem severe. Avoiding them, however is simply a matter of being honest and forthcoming about your email content. While some clever marketing tactics may lead you to “Walk the Line,” when it comes to email, it’s always best to remember the golden rule – Which, it turns out, is actually the best rule for anything online.