A re-engagement email and win-backs help your newsletter avoid spam traps

person reclining in a park

We know that a trustworthy newsletter makes it easy for people to unsubscribe. But what about the people on your list who have ghosted your newsletter? That’s why you need a re-engagement email.

Some subscribers engaged for a bit, but they haven’t opened, read or clicked a single email in weeks. Or months. If you’re thinking “or years”, this post is definitely for you.

What percentage of your list hasn’t opened an email in 9 months or longer? 5%? 25%? Be honest, it’s okay.

You will lose 20-30% of your list every year. People get cluttered inboxes. They move out of your area. They only wanted a special offer. Their circumstances change. It’s a fact of life.

Inbox providers like Gmail, Yahoo or Outlook keep tabs on inactive inboxes. Let’s say someone hasn’t logged into their email for two years.

When you send your newsletter to this inactive email address, it shows inbox providers you don’t keep a clean mailing list.

You know who else doesn’t keep clean mailing lists? Spammers.

That’s a major problem. If you don’t take list hygiene seriously, it’s going to screw your deliverability big time. If your email provider charges you based on your number of subscribers, then your list is costing you more for worse performance.

I have good news though. You don’t have to scrub every inactive subscriber off today. We’re gonna win some subscribers back.

The re-engagement email

The re-engagement email is exactly what it says on the tin. It’s a very brief email you send to your dormant subscribers to make sure they are still there, and keep you on their radar.

Quick note: In this post, I also use the term win-back email. A win-back email is similar to a re-engagement email, with slight differences.

Ideally, you will send 2-3 re-engagement emails. After all, if a subscriber hasn’t ignored you for 6 months, there’s a pretty minimal chance they will jump at your first attempt.

But again, I have good news. In a study by Return Path, 45% of subscribers who received win-back messages read subsequent emails (PDF link). Here’s the kicker: only 24% of those people read the win-back email.

That’s bananas! In this study, people who didn’t even read the win-back email started opening emails again.

I need to manage your expectations here. The re-engagement email isn’t going to jumpstart all your inactive subscribers. Chances are, the open rate on the re-engagement email is going to be lower than your list average — and that’s okay.

The value is retaining subscribers who lapsed but are still interested. Retention is incredibly important for building loyal audiences. Depending on whom you ask, a new customer costs 5x-25x to get versus keeping an existing customer.

In a world relying more on reader revenue and paid subscriptions, retention can’t be a secondary goal. Subscriber churn devours startups before they even know what hit them. Churn bogs down an established newsroom like quicksand — the more you fight the deeper you sink.

Before you write your re-engagement email, define what inactive means.

There is no one-size-fits-all re-engagement email formula. Defining your goals and your terms is the most important place to start. You have to do this first.

Your approach changes based on what your newsletter’s goals are, and the frequency. Without these two pieces, you can’t define “inactive”.

For example, if your newsletter is designed to drive revenue, “inactive” should tie to the last order or donation. Keep in mind that higher orders have a longer lead time than small orders.

On the other hand, newsletters driving clicks to your site should use indicators like the last time they opened or clicked an email.

Newsletter frequency needs to be considered in your “inactive” definition. Let’s say Newsletter A goes out every day, and Newsletter B sends once a month. If a subscriber is inactive for 9 months, that’s 273 emails of Newsletter A, but only 9 emails of Newsletter B.

It’s easy to think “oh, they haven’t responded for 9 months, so we’ve lost them”.

It’s important to follow up and talk to inactive subscribers. People may have good reasons why they aren’t engaging, and they may reveal opportunities you weren’t seeing.

Pick one action. Only one.

Your goal with a win-back is to figure out if this subscriber is still on the other end of the line. That’s it.

There are only three ways this will go: Yes, No and Silence.

To capture the Yes people, give them a nice big “Yes, I still want to get your emails” button. For the no people, don’t ask them to manage their preferences. Make it easy for them unsubscribe, or better yet, let them know you will take care of it.

If you have multiple newsletters, give them an opportunity to change the frequency. You make keep some by letting them change from daily to weekly.

Truthfully, most of these inactive subscribers will fall into the Silence category. What’s next for them?

For starters, keep that Return Path study in mind. There are some people who don’t open or engage with the win-back email who will start opening emails again. Think of them as a delayed “yes”. These count toward your success!

Timing is important; don’t jump the gun

As a general rule, inbox providers consider an address inactive if the owner hasn’t logged in for 12 months. After that 12 months, each email you send risks getting you on their spam radar.

But there’s another part of the Return Path report that is interesting. The average time it took from win-back email to reading a later email was 57 days. Almost two months!

Give yourself a buffer between sending your re-engagement email and scrubbing your list. As long as you don’t zoom too far past the 12 month marker, you may pick up a few more hibernating subscribers.

During that buffer period, you should send more than one re-engagement email. I suggest 2-3. They aren’t opening your emails, so you probably aren’t going to get their attention in one shot.

What does this look like? With a daily newsletter, 6 months of unopened emails is probably plenty. Send them a win-back after 5 months, then again at month 7 and a couple weeks after that. If they still haven’t opened anything by month 9, scrub them.

That’s not super aggressive, and it’s manageable. Your results may vary, and you should test this. In fact, as you establish good list hygeine, you may find you benefit from a shorter or longer schedule.

Avoid the urge to be a comedian

One of the hottest — and stupidest — trends today is the use of needy patterns. You’ve seen them as links under call-to-action buttons, usually something like “No, I hate saving money” or “No thanks, I don’t like to learn things”.

"I'd look like a real jerk if I said 'No'"

Even if these get more conversions, they are not worth it. They are rude and unnecessary. Building loyalty is a long-term game, and needy patterns are cheap shortcuts.

A lot of win-back emails from retailers take on a tone of of a break-up. That may work for retailers, but it’s often comes across as silly. Be straightforward and user-focused.

What should your re-engagement email say?

This is normally where I share examples from the 99 Newsletters. I’m opening and re-opening and clicking on emails in the 99 Newsletters, so I don’t have any win-back emails to share.

So we have to improvise a bit with a re-engagement email from James Clear, author of Atomic Habits.

This one came on a super short lead time — about a month after I signed up. I guess James likes to keep a sparkling clean list!

James does three things in this email that I really like:

  1. He is respectful of your time and your inbox, in those words. “I want to make sure I’m not wasting your time by sending you emails you don’t want.”
  2. One action for the reader. If you want to keep getting emails, click the one link in the email. It’s even in bold. I like buttons better, but this is great.
  3. If you don’t want more emails, you don’t have to do anything. You’ll automatically be removed. Not your problem to solve.

I don’t even think you need to say this much, especially the paragraph about the email software. Most likely your subscribers know they ghosted, or they are using your newsletter for other purposes.

For your email, this is a great opportunity to mention any big improvements you’ve made. Maybe you unveiled a more user-friendly design, or got rid of autoplaying video ads everyone hates. If you fixed something, don’t feel you need to hide it. Being honest about what you fixed may overcome their reluctance to come back.

You could also mention a big new initiative that’s gaining traction, or an award winning story.

But you can only pick one thing.

One thing. Seriously. If they haven’t read the last 273 newsletters, they for damn sure aren’t reading your list of 273 things you think they missed.

Be careful offering discounts as bait

There are only two ways to increase revenue:

  1. Sell to more customers
  2. Sell more units to your existing customers

Subscription businesses without tiers must do Option 1: find more people to buy subscriptions. It doesn’t do most people any good to have four subscriptions to the same news site.

Retailers often use coupons or discount codes to win back customers who haven’t ordered in a while. That works for retailers, but it can be an uphill road for publishers.

Why is it an uphill road? For starters, it conditions people to wait for the deepest discount. They take the good offer, and they are more likely to cancel at the end of the cheap rate. It creates a vicious cycle when budgets are tight enough.

It also comes across as desperate. In the past month, the New York Times has sent me ten “special offers” to subscribe. TEN. That’s one every three days. One one day, they sent me two offers less than 12 hours apart. The same day!

I didn’t open any of them until I started researching this post, because I’m not interested. When I counted up all the offers – I was less interested. And the sheer repetitiveness shows these offers aren’t special at all. They are just cheap.

Don’t copy the New York Times. This is not how you do win-back emails.

Segmentation makes re-engagement more effective

Re-engagement and win-backs get a huge boost from segmented lists. People lose interest for different reasons, so they aren’t going to be re-engaged for the same reason.

An up-to-date segmented list gives you flexibility. Segments position your win-back around your readers’ interests or previous purchases.

Segmentation doesn’t have to be complicated or technical, either. Start small and work your way up.

What if you segmented your list by paying subscribers, former subscribers and non-subscribers? Each group has a different relationship with you. Approach them in the appropriate context.

Disengaged paying subscribers may love a discount offer. Offering a non-subscriber a steep discount could lead to high turnover, short-term subscribers. High churn costs you more in the long run.

The key is testing small batches as much as you can to figure out what works. Confirm your findings, review your strategy regularly and keep doing what works.

I know a lot of newsletters aren’t segmenting lists, probably because they aren’t sure where to start. I’m not here to shame. If getting started with segmentation has been on your radar, shoot me an email and we can talk about getting you up and running.


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Don’t sabotage yourself! Make it easy for people unsubscribe from your newsletter

overflowing mailbox

Watching people unsubscribe from your newsletter sucks.

How much it sucks increases as you put more work into it. It’s hard to watch unsubscribes dampen your projections in a world where striving for scale eats up so much attention.

I’ve been analyzing the design of the 99 newsletters, and I needed to unsubscribe from one. Someone had added me to a new newsletter that I never signed up for (please don’t do that).

When I struggled to unsubscribe, I saw newsletters pulling out all the stops to keep me from leaving. This will backfire big time.

This industry is tough enough as it is. Let’s not sabotage ourselves.

Make good choices that benefit users

Obscuring your unsubscribe link is a choice.

When you choose to hide your unsubscribe link:

  • You are begging to get marked as spam.
  • You damage your deliverability.
  • You harm your standing with your readers.

None of those are worth it! But there’s more: hiding your unsubscribe link makes it harder to learn what’s resonating with readers. It’s a textbook case of shooting yourself in the foot.

Your list is going to degrade over time. People churn out for reasons you can’t change: they move, they change jobs, and even when they die.

The solution isn’t to make it harder for them to leave. Instead, focus on acquiring high quality new subscribers, deliver value to move them through your funnel and build loyalty. One loyal reader is worth 1,000 (or more) disengaged subscribers.

Let people unsubscribe from your newsletter

Checked out subscribers on your list are holding you back from your newsletter goals. Let them unsubscribe. Better yet, make it easy to unsubscribe.

According to Litmus, 50% of consumers mark an email as spam because it is confusing or painful to unsubscribe.

This is important because spam complaints harm your deliverability. Unsubscribes do not. Moreover, spam complaints have a ripple effect. It doesn’t only apply to the person who marked it as spam.

When the mailbox provider starts noticing spam complaints, they start filtering your emails. The filter isn’t limited to person who flagged it. It’s affects everyone. That spam filter eventually will catch all your Yahoo subscribers. Or all your Gmail subscribers. That’s way worse than the Promotions tab.

The takeaway: if you don’t want users to find the unsubscribe button, then you want to frustrate them. And you want them to mark you as spam. That’s definitely not what we want, so let’s look at easy ways to fix it.

Make it easy to unsubscribe

The first step to making it easy to unsubscribe is using that specific word: unsubscribe. That’s what your disengaged reader wants to do, so use the word.

Euphemisms and corporate speak don’t help your readers. No one wants to “manage their preferences”.

Another thing I’ve seen is people linking to words that aren’t “unsubscribe”. There’s no need to be clever or helpful by highlighting words other than unsubscribe, like “click here” or the user’s email address. Give the people what they want.

Constant Contact uses their trademarked term “SafeUnsubscribe™”. I recommend changing it to “unsubscribe”. People aren’t looking for a word Constant Contact made up.

Put the unsubscribe link at the bottom

People look for unsubscribe links at the bottom, so put it there. If you have one at the top or in the body of the email — great! Put another one at the bottom to cover your bases.

Make the unsubscribe link stand out

Now that your newsletter says “unsubscribe” at the bottom. What’s next?

Draw attention to it:

  • Increase the type size
  • Make it bolder and higher contrast.
  • Underline it.
  • Separate it from other elements, especially text.

You should do all four of these. At the very least, do three of them. It should be obvious it’s a link. If you make it high contrast and bold, then it’s not 100% necessary to underline it.

Roanoke Times unsubscribe link
Adding a second link in all caps at the absolute bottom is a nice precaution.

This example from the Roanoke Times does the job. Unsubscribe is pulled out from the big block of text before it. It’s the first choice in the line. It’s bold and it’s blue. And just in case you scroll too fast, there’s a second UNSUBSCRIBE at the very bottom.

Make the font size bigger

My only minor quibble with the Roanoke Times example is the type is a little small. However, the combination of putting unsubscribe on its own line, making it bold and making it blue keep it easy to spot and click.

The median font size for the unsubscribe links in the 99 Newsletters is 13 pixels. Some ae as small as 9 px, which is way too small. The largest is 16.25 px, nice and large. I wouldn’t go smaller than 14 px, and 16 px is even better.

Don’t worry. Loyal readers aren’t going to be so entranced by your unsubscribe link that they click it. If this worries you, add a link on the unsubscribe page telling people how to resubscribe.

Our friends at the Arkansas Democrat Gazette handle this nicely:

People looking to stop receiving emails will thank you for letting them unsubscribe easily (even though they aren’t going to tell you). They will thank you by not reporting you as spam. Or resubscribing later!

Make sure unsubscribe stands out on mobile

A lot of unsubscribe links end up in the fine print of the footer. Fine print is already challenging on desktop; it’s much harder to tap a tiny link with your finger.

It should be easy to tap the unsubscribe link on a phone. On mobile, it’s important to separate the unsubscribe link from other text and links in the footer.

Let’s look at some good examples you can copy:

VT Digger, a nonprofit newsroom in Vermont, doesn’t reinvent the wheel. They make the font size nice and big, and styled it like a link. This is nothing more than helpful styling added to standard Mailchimp verbiage. Mailchimp accounts for 52.5% of the 99 Newsletters, so I saw a lot of straight out-of-the-box footers.

VT Digger unsubscribe link

Next up, the New Hampshire Union Leader. Again, nothing fancy that you can’t steal. The Unsubscribe is on it’s own line, in the blue link color, bold & underline. It’s easy to tap with a finger, and not hit that address that will throw you into Maps.

Unsubscribe link from New Hampshire Union Leader

Last but certainly not least is the Weekender from inewsource.org in San Diego. This red button is easy to see and tap on a phone, even if I wish the type were a bit larger.

Unsubscribe button from inewsource.org

Note the second marker. There’s also a link to unsubscribe from everything. A nice touch!


Don’t annoy people with your preferences page

The best option for handling unsubscribes is the effortless one-click unsubscribe. It solves the problem with the least amount of effort for your users.

The Brief from Texas Tribune goes one step better. Like inewsource.org, they give you the link to unsubscribe to everything right there in the email.

Texas Tribune newsletter unsubscribe
This gives the user options. Unsubscribe from this newsletter, or get all of them unsubscribed at once.

That’s a boss move. It helps keep the Tribune list clean. It takes a lot of confidence, but you can do this, too.

But what if you have a bunch of newsletters, or your email provider doesn’t make global unsubscribe easy? In that case, you need to make the unsubscribe page as straightforward as possible.

The most user friendly option puts “unsubscribe from all newsletters” right at the top of the page. None of the 99 newsletters do this.

If you aren’t struggling with spam complaints, and you aren’t experiencing deliverability problems, then you’re probably okay. I would keep an eye on it, especially when you get big waves of new subscribers.

Don’t force people to login to unsubscribe.

If you don’t use an “unsubscribe from all” link like Texas Tribune, then you use the Manage Preferences page, or something similar.

This step is unnecessary. You have their email address. You are asking users to jump through hoops, and they will not be happy about it.

Only 1 newsletter required a login to Manage Subscriptions: The New York Times.

New York Times login screen
The newspaper of *record scratch*

Slightly more common (14.8%) are unsubscribe pages that weren’t clear. For six newsletters, it isn’t clear if you unsubscribe from one newsletter or all newsletters. Five others make the “unsubscribe from all” option very hard to see.

A whopping 30.5% of publications do not offer users the option to unsubscribe from everything. That’s disappointing.

Put yourself in a reader’s shoes. You know what it feels like when you can’t figure out how to get off a mailing list. You understand how it feels like cheating when a retailer unsubscribes you from one list, but not another list you never realized you were on. Let’s not do that to people. We want them to trust us.


Arkansas Online is the website for the Arkansas Democrat-Gazette in Little Rock. Their preferences page could use some work. Let’s take a look at it.

(1) I’m subscribed to the Midday Update. I can figure out that AO stands for Arkansas Online, but wouldn’t it be helpful to spell it out? You have to show readers what they need to do.

The dropdown says “Yes”. So far so good. I can change it to “No”, which presumably would unsubscribe me. But wait…

(2) What are these checkboxes for? I came here to unsubscribe. Do I check the boxes I want to unsubscribe to? Do I check the boxes for new newsletters I want to get? What happens if I put “No” above, but check the box here?

I have no idea. I’ll guarantee you users aren’t going to spend more than two seconds trying to figure it out.

To add insult to injury, (3) here’s the “unsubscribe from all” link hiding below the save changes button. This is a very long page I cropped. Then way down here, a link. In light grey that’s hard to read.

It’s important to walk through these steps before you launch, and re-visit them regularly. Time yourself doing it. I bet it takes longer than you think — and you know the right answers!

Oh — one more thing. Don’t send that “unsubscribe confirmation” email if you can help it. It’s the 64-inch CVS receipt of email newsletters.


A healthy mailing list works harder for you

If you have a list of 130,000 subscribers, but 30,000 haven’t opened any emails over the past six months — what’s the value there?

What’s the value for them? You’re sending them something every day that doesn’t get looked at, much less read.

What’s the value for you? They aren’t reading your messages, and they aren’t engaging with your content. It’s about as effective as donning your newsboy cap and yelling headlines on a quiet street corner.

What’s worse is they are dragging your numbers down. If your open rate is 19% on 130,000, scrubbing those 30,000 inactive accounts bumps you up to 24.7%.

Granted, I don’t think Open Rate is the top metric you should focus on. But I bet there’s at least one upper level manager excited to see a 5.7% increase on the opens report.

The real value of more accurate measurements is you’ll learn more. You gather clearer insights when you don’t have data clouded by inactive subscribers.

When you have clearer insights, you can deliver more value to the people who love your newsletter.

Your newsletter is a relationship between you and a reader. Allowing them to go shows that you respect their time and attention. Making it easy gives them a reason to trust you. Doing right by your users is an investment that pays off every time.


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