Winback Emails: How to Bring Back Customers Who Stopped Buying

Winback emails go to customers who used to buy from you and have stopped. They're the last automated flow most stores set up, and often the one that gets the least thought. A good winback flow is short: two or three emails, sent once a customer is clearly overdue for their next order, giving them a real reason to come back before you reach for a discount.

You're not starting from zero with these people. They've bought before, they know what arrives and how it feels. You just need to remind them, and give them a reason that isn't "please".

When should you send winback emails?

When a customer is overdue, which is different for every store. Someone buying coffee beans might reorder every three or four weeks. Someone who bought a sofa might not need you again for years, and a winback flow makes little sense for them at all.

Look at your own order history. Find the typical gap between a customer's first and second order, then start the flow a little after that. If most repeat buyers come back within 45 days, someone who's been quiet for 60 has probably drifted. If the usual gap is four months, start later.

Some platforms, Klaviyo included, can estimate when each customer is likely to order next. That's worth using once you have enough order data. Until then, a trigger based on your own typical reorder gap works fine. I'd rather see that than a default "90 days since last order" copied from a template.

How many winback emails should you send?

Two or three, spaced about a week apart.

Email	When	What it does
1	Once they're overdue	Something useful or new, no discount
2	About a week later	A reason to trust you again: reviews, what's changed, an easy reorder
3 (optional)	About a week after that	The offer or the honest "should we stop emailing you?"

Anyone who buys at any point should leave the flow straight away. Check that before it goes live. Getting "we miss you!" the day after an order looks careless.

What should winback emails say?

Email 1: lead with something worth opening

Not "We miss you". Everyone sends that, and it's about you, not them. Open with something they'd care about: a new flavour or size, a restock of what they bought last time, or a simple reorder button for the product they had.

Subject: your usual's back in stock

The medium roast you ordered in the summer sold out for a few weeks. It's back now, roasted on Monday. One click reorders the same bag, same grind.

Short and specific is the goal. If you can reference what they bought, do. It's the main advantage you have over a cold email.

Email 2: remind them why they bought

Some people drift away because life got busy. Others had a small problem: a late delivery, a product that wasn't quite right. You can't know which, so make it easy either way. Show a few genuine reviews, mention anything you've improved (faster delivery, a new returns policy), and invite a reply.

If something put you off last time, hit reply and tell us. It goes to a real person, and we'd honestly like to know.

That last line does more than it looks. Replies tell you why customers leave, which is useful long after this flow.

Email 3: the offer, or the honest question

If you use a discount anywhere in the flow, put it here. By now the customer hasn't responded to the product or to reassurance, so an incentive has a job to do. Keep it simple and time-limited, and make sure it's something you'd be happy to honour.

The other option is to skip the discount and ask directly whether they still want your emails. It feels risky, but it's honest, and it keeps your list clean.

When should you stop emailing someone?

If a customer has ignored the whole winback flow, take that as an answer. Move them to a "sunset" segment that gets fewer emails, or none, rather than mailing them every campaign for another year.

It feels wrong to shrink your list on purpose. But people who never open hurt your sender reputation, which can push your emails into spam for the customers who do want them. A smaller list that reads your emails is worth more than a big one that doesn't.

Common winback mistakes

• Starting with the biggest discount you'll ever offer. It trains customers to go quiet and wait for it.
• Same trigger for every product. A 90-day rule makes no sense if you sell both monthly refills and one-off furniture. Split the flow if your products have very different reorder cycles.
• Sending it to people who just bought. Always check for recent orders before every email.
• Long emails. These customers need a nudge and a reason, not a newsletter.
• No plan for people who don't respond. Without a sunset step, the flow just leaks unengaged contacts into every campaign.

Winback works best as part of a set. If your welcome sequence and abandoned cart emails aren't in place yet, start there, then add this. My guide to email flows that convert covers the order I'd build them in.

Frequently asked questions

What is a winback email?

It's an automated email sent to a customer who has bought before but hasn't ordered for longer than usual. The aim is to bring them back before they forget about you completely.

Should winback emails include a discount?

Not in the first email. Start with something useful or new, and keep any offer for the last email in the flow, if you use one at all. Leading with a discount teaches customers to wait for it.

How long after the last purchase should a winback email go out?

A bit longer than your customers' usual gap between orders. Check your own order history; for fast-repeat products that might be a few weeks, for others a few months.

If you'd like your winback flow planned and written alongside your other lifecycle emails, have a look at my email lifecycle strategy service or get in touch. If your flows already run in Klaviyo and you only need the emails written, Klaviyo copywriting is the smaller project.