Confessions from Email Prison

In our last MarTech column, “Don't do it! Or you'll end up in email jail,” we listed 10 crimes that can land a digital marketer in email jail. They range from minor offenses like sending a transactional email without a single business-building sales pitch to more serious offenses like buying lists and skipping authentication.

No discussion of email misconduct would be complete without weaving in a few prison confessions to support my claim that we've all committed some kind of marketing infraction at some point, either because we didn't know any better, we were desperate, or someone (like a boss) forced us to do it.

These excuses may not hold up in the eyes of blocklist judges or the heads of ISPs, but we can all take some solace in knowing that anyone can end up on email's most wanted list.

Everyone needs to fix something

This is where many email senders turn into marketing thugs. I've worked in the email industry for 26 years, working with a wide variety of companies, from one- or two-person businesses to large international corporations, and I've seen this happen all the time. Every company is different, and everyone I meet needs some help.

I often become a corporate email lawyer as an outsider with a fresh perspective and broader understanding of what’s going on in the world of digital messaging. I’m not tied to office politics and I’m focused on helping companies succeed by following the law.

I've witnessed a lot of email abuse, both inadvertent and intentional, and a lot of work has been done to clean it up and get companies out of email prison. I've shared some stories below that I hope will inspire you to improve your own processes and set goals to fix potential evasions of laws, whether those laws are actual statutes like CAN-SPAM (US), CASL (Canada), GDPR (EU), or generally accepted best practices like permissions.

Four confessions from email prison

1. Buy a list

In the United States, buying lists for email marketing is not technically illegal, but it does violate many email practices, including permissions and consent.

Confession

Being an avid golfer, I was excited to work with a well-known golf equipment manufacturer. I soon learned that the CEO had paid a six-figure amount for a list of millions of names and email addresses. And they were super excited about it.

During our initial conversation, I heard some grand predictions about how this massive list would impact their business, and they wanted me to help them spread their message and acquire tons of new customers.

In reality, that didn't happen, and over the next two weeks I met with people from the company multiple times to explain the specific metrics of how they lost a lot of money, including the amount the CEO spent to acquire the addresses, as well as the upfront costs of validating all those millions of addresses.

We also clearly explained the reaction from customers (not much), the spam reports (a lot), the sales (much less than expected) and the impact on sending domains (huge damage).

I said I could expect about $23,000 in return from the six figures I spent on the listing. They disagreed. That was the last time I worked for that company.

lesson

I haven't heard of them using that unverified list to launch a campaign, but this highlights one of the penalties of being in email jail: you're paying for something that never brings you the return you expect.

People buy and use email lists every day because it’s easy to do, they don’t realize the results, but you know it now.

Learn more: 4 best practices for building a clean, attractive email database

2. Sending emails to unsubscribed addresses

One of my previous companies was a multi-channel international retailer. We had a very structured in-house email team of eight people and an extended agency team. But being in retail, we were always working at full speed, and during the holiday season, it really accelerated. We were forced to become very tactical email marketers. Our job was to get campaigns out there.

CAN-SPAM had just become law in the US and my company met with the Federal Trade Commission, which administers the CAN-SPAM Act regulations. Google's Gmail was not yet as powerful as it is today. Deliverability was important then, but most people didn't pay as much attention to protecting deliverability as they do today.

Confession

A colleague came into my office and slammed the door. In a panic, she confessed that she had just sent a massive campaign to a custom list that included every email address that had unsubscribed. Not just the most recent ones, but all of them.

I had just come across CAN-SPAM and my panic was at an all-time high. We weren't just breaking a nice-to-have best practice; we were breaking the law. The law.

How did this happen? We didn't follow a clear process to make sure we were sending to the right list. As it happened, the segmented list that our data tech pulled for her campaign included unsubscribers. We should have realized that the list was too large for the segment she specified, but in our rush to send, we missed that obvious detail.

So who ended up spending time in email jail because of that? Luckily, no one. We got the equivalent of a warning and being fired. No one said anything. There were no spam complaints explosions. No one got fired. But that was 2004. What if it happened today? It's scary to think about.

lesson

No matter how big your email program is or how fast you have to move, you need to slow down and put processes in place to prevent these incidents from happening again.

But the thought of it still makes me sweat a little.

3. Sending emails to hard-bounced addresses

A friend of mine worked for a B2B publisher with a total mailing list of about 100,000 addresses (maybe 20% were active). He and his boss noticed a steady decline in opens and clicks, and a sharp increase in hard-bounced (permanently undeliverable) addresses. This trend accelerated after the 2008 recession, when many in his industry were laid off as teams were downsized or eliminated.

As you know, the usual practice is to delete and isolate hard-bounce addresses so you don't risk incurring the wrath of ISPs or blocklists by sending email to them. Their email platform automatically deleted these addresses and sent them to a suppression list. As a result, emails were only resent to soft-bounce addresses three times before being deleted.

Confession

Up until this point, the list hygiene process was going well. But then the publisher became suspicious and wondered how many of the undeliverable email addresses were false positives, or addresses that were incorrectly classified as undeliverable. Against almost everyone's advice, he had his data team create a mailing list from the do-not-send file and send the newsletter to that list.

The result? A few opens (probably bots). A few clicks (also likely bots). No significant change in engagement. The sending IP gets added to at least one major blocklist, and there are who knows how many ISP filters with “undeliverable” warnings.

lesson

If an email address comes back as undeliverable, believe it – the cost of checking just to be sure is too high.

Learn more: Modern email marketing: Data privacy, bulk email limits, and more

4. Change everything based on one campaign

When I was working with another large national brand, someone thought it would be a great idea to ditch the complicated HTML templates and send one campaign all as text emails. Why? Because I read an article where another brand had done it and their click-through rates were astronomical.

Yes, it was high because the email was different. It was novel. It was a change from the usual template, so it stood out. That's what made it stand out. With careful planning and the use of one-off designs, you can create an effective campaign.

Confession

The first few campaigns were successful enough. But then the executive committed his first felony. He used the results of the one-off incident to change the entire program. Predictably, the novelty wore off, the numbers dropped, and the email team went back to HTML templates.

This landed him a second prison term for email charges and cost the program money because he acted on false information.

lesson

Always test and retest to validate your findings. Make sure what you're testing is accurate based on your hypotheses. Be wary of sudden changes that may let novelty influence your results rather than a data-proven strategy.

summary

These discussions of email jail are a reminder that email marketing, like any other marketing channel, has a set of rules — and if you don’t follow those rules, you’ll face real consequences, like being denied access to the inbox.

In the early days, you could claim ignorance because we were all learning and many of the rules we follow now were unwritten back then. Penalties didn't exist or weren't as severe. But ignorance of the law is no longer an excuse.

The thought leadership addressing these issues is the equivalent of the world’s largest email law library – as close as a MarTech archive or a Google search.

The email frenzy of Q4 (yes, that happened to us) might have you wondering how to get out of email prison. Help is available – just ask.

What I don't recommend is the old way to avoid email jail: sending donuts to ISP security guards.

When I started my career, AOL was one of the big mailbox providers that we had to keep happy. In the early days of delivery, if the sender wasn't on the white list, they wouldn't get it to the inbox. I knew the postmaster at AOL, and I used to send her gift certificates to keep us on the “preferred” list.

Yes, that was a bribe. And no, don't do that to your current postmaster, unless you know his or her dress size, favorite wine, or the age of their kids. And even then, maybe not. Following the rules of email is your best bet to stay out of email jail.