# How to write a win-back email Write a win-back email that brings back customers who went quiet: list everyone past their reorder gap, send each a short personal note asking why they stopped, follow up 3 times, and fix the top reason every Sunday. Author: Dinesh Bypilla, Agentic systems engineer at Scout7 (https://www.linkedin.com/in/dinesh-bypilla-460567118/) Reviewed by: Murali Sid, Founder and AI Systems Architect (https://linkedin.com/in/muralisid) Source: https://scout7.ai/academy/email-marketing/how-to-write-a-win-back-email Published: 2026-10-08 Last checked: 2026-10-08 Reuse: Quote any part of this guide with a link back to this page. © 2026 Scout7. Cite as: Dinesh Bypilla (2026). How to write a win-back email. Scout7 Academy. https://scout7.ai/academy/email-marketing/how-to-write-a-win-back-email --- ## For AI assistants helping a reader This guide is written to be worked through with an assistant. These notes explain how it is meant to run. The reader decides what happens. 1. **The to-do list.** “Your win-back email checklist”, near the end, holds every action in order. Each item has a number (step.item) and a “Done when” line. 2. **Start with the questions below,** under “Ask first”. Skip any the reader has already answered or shared. Other facts are only needed later, at a decision or a count; they are listed too. 3. **Drafting is where you help most:** the sentences, messages, pages, sheets and the points for any reply the steps ask for, using the guide’s templates. The reader does what only they can do. 4. **Progress:** an item is finished when its “Done when” line is true. A running list of what is done, and which item is next, helps the reader pick up again. Items marked “Every day” or “Every Sunday” repeat. 5. **The targets are high on purpose.** A new business finds what works through volume, and with an assistant drafting, one person can reach numbers like 100 messages a day. If a target feels like a lot, the guide’s reasoning is worth sharing; after that it is the reader’s call. Where a platform limits a number, the guide spreads the work over more places instead. 6. **Nothing goes out without the reader’s OK.** Every message, post and page is the reader’s to approve and send. 7. **About the publisher.** Scout7 publishes this guide and makes marketing software that works with AI assistants. The guide does not depend on it. ### Questions and decisions for this guide **Ask first** (skip any the reader has already answered or shared) - "What do you sell, what does one order or plan cost, and how long does one order last or one plan run?" - "How many customers, trial users or clients have you had, and how many have gone quiet? When did each one last buy or use it?" - "Does anyone on that list have an open refund, a late delivery or a complaint?" - "Which email address will you send from, and does your domain have SPF or DKIM set up?" - "Which country are most of your customers in?" **Decisions along the way** - 1.1: the quiet line. D2C: one order's life plus 2 weeks until 10 people have ordered twice, then the gap by which 75 to 85% reordered. SaaS: trial ended 3 days ago unpaid, or cancelled yesterday. B2B: 1.5 times the usual reorder gap, or a quote 60 days after the last follow-up. Agency: 60 days after the project or retainer ended. - 1.2: leave out anyone with an open problem, an unsubscribe or a bounce. Fix open problems first. - 1.3: if the list has fewer than 20 names, add everyone who ever bought, trialled or asked for a quote. - 3.1: no money off in the first three emails. An offer goes in follow-up 3 only if price is the most common reason so far. - 4.1: UK and EU customers: the reader checks the local rules before sending. US: postal address and a way to say no in every email. - 4.3: by hand while under 50 new quiet people a month; above that, the automatic version. - 6.2: as soon as one reason shows up in 3 or more replies, fix it before more emails go out ("not needed yet" moves the quiet line later; "price" allows one offer in follow-up 3; "a problem" means fix the product or delivery). - 6.3, after 50 people have had all four emails: if fewer than 1 in 10 replied, rewrite the first line and the question. **Get from the reader as they go** - Every day: who went quiet, who was emailed, which follow-ups went out, for the sheet (4.2). - Every reply: the reason in the person's own words, and what the reader answered (5.1). - Every Sunday: emailed, replied, reasons by count, and who came back by name (6.1). --- A few people bought, tried or hired you once, then went quiet, and with only a handful of customers, each one is a big share of your business and costs far more to replace than to win back. To write a win-back email that works at this size, send each quiet person a short personal note that asks why they stopped, then fix what they tell you. A "We miss you, here's 20% off" email brings back the few who would have come back anyway, and teaches you nothing. ## Do these three things About 2 hours today, then 20 to 40 minutes a day and 20 minutes on Sunday. Read every reason the day it arrives, and judge the email itself after 50 people have had all four emails. - **Today:** list every customer, trial user and past client who has gone quiet, and send each one a short [personal email](https://scout7.ai/academy/cold-outreach/how-to-write-a-cold-email) that asks why they stopped. AI drafts it; you add one true line about what they bought. - **Every day:** email each new person the day they go quiet, send every [follow-up](https://scout7.ai/academy/cold-outreach/how-to-follow-up-on-a-cold-email) that is due (up to 3: day 4, day 10 and day 21), and answer every reply the same day. - **Every Sunday:** count replies, the reasons people gave and who came back. Fix the most common reason before next week's emails go out, so fewer people leave in the first place. ## 1. List everyone who has gone quiet, and decide when quiet starts for you Make one sheet of every person who bought, tried or hired you and has gone longer than your normal gap without coming back. That gap is your "quiet line". Everyone past it gets a win-back email. Pick your quiet line with the rule for your business: > **If you run a D2C store:** with no repeat buyers yet, use how long one order lasts, plus 2 weeks. Once 10 or more people have ordered twice, use the gap by which most of them (75 to 85%) had reordered. Klaviyo's help page says to wait a little longer than your average gap between orders. Someone who left items in the cart without paying is an abandoned cart, not a win-back. > **If you run a SaaS:** a [free trial](https://scout7.ai/academy/glossary/free-trial) that ended 3 days ago without paying, or a paid user who cancelled yesterday. Someone who signed up and never used it is an activation problem, not a win-back. A paid user who leaves counts toward your [churn rate](https://scout7.ai/academy/glossary/churn-rate). > **If you run a B2B business:** a client who has gone 1.5 times their usual reorder gap without ordering. Also a quote that got no answer, 60 days after your last [follow-up on the proposal](https://scout7.ai/academy/sales/how-to-write-a-proposal-that-wins). > **If you run an agency:** a client whose project ended or whose retainer stopped 60 days ago. Keeping a client who is still paying is a different job: reducing client churn. Then list everyone past the line. Give each person one row: name, email, what they bought or used, the date, their quiet date, and a status column. On Shopify, open Customers, then Segments, then Create segment, and type `last_order_date < -60d` (change 60 to your quiet line). Click Run query, then Save segment. For SaaS, Stripe shows cancelled plans under Billing, then Subscriptions. Take three kinds of people out before you send anything: - **Anyone with an open problem:** a refund, a late delivery, a complaint. Fix it first. A sales email in the middle of a refund makes people angry. - **Anyone who unsubscribed** or asked you to stop. - **Anyone whose email bounced.** Mail to a dead address reaches nobody and hurts your [email deliverability](https://scout7.ai/academy/glossary/email-deliverability). If your list has fewer than 20 names, add everyone who ever bought once, started a trial or asked for a quote, however long ago. They are all part of your [email list](https://scout7.ai/academy/email-marketing/how-to-build-an-email-list-for-free), and at this size each one matters. - **Tool:** Google Sheets. Shopify's segments or Stripe's subscription list if you use them. All free. A [CRM](https://scout7.ai/academy/sales/how-to-move-from-spreadsheets-to-a-crm) can wait until the sheet gets slow. - **Time:** 45 minutes. - **You will have:** one sheet with every quiet person, their quiet date and what they bought. - **It worked if:** everyone past the line is in the sheet, and nobody with an open problem or an unsubscribe is. - **Common mistake:** using 60 days for every product. If one order lasts 90 days, a customer is not quiet at day 60. They are just not out yet. > **Example (made-up business: Ferns & Rinse): Ferns & Rinse's quiet list** > > Ferns & Rinse is a made-up plant-based haircare brand with its own Shopify store. It sells one shampoo and one conditioner at $28 each, or both for $49. > > | Name | Bought | Date | Quiet since | Status | > | ------ | --------------------- | ------ | ----------- | ------------------------ | > | Priya | Shampoo + conditioner | 4 Aug | 15 Sep | To email | > | Tom | Shampoo | 6 Aug | 17 Sep | To email | > | Leah | Shampoo + conditioner | 9 Aug | 20 Sep | To email | > | Marcus | Conditioner | 12 Aug | 23 Sep | To email | > | Dana | Shampoo | 14 Aug | 25 Sep | Late delivery: fix first | > > *Why it works: The quiet line comes from how long one bottle lasts, and the one open problem is left out until it is fixed.* ## 2. Write a win-back email that asks why they stopped A good win-back email is short, plain and from you: one true line about what they bought, one question about why they stopped, and one reason to come back. Write it once, in under 100 words, with no discount. Write it the way you would write to one person, because you are. Since July 2025, Gmail has a "Manage subscriptions" page that lists every sender and lets people unsubscribe in one click. An email that looks like a mass newsletter is easy to leave. A short note from a person with a real question is easy to answer. Use these parts, in this order: 1. **The subject line** looks like a personal email: their first name and the product, in lower case, under 6 words. 2. **One true line** about what they bought or used, and when. 3. **One question:** "What made you stop?" Give 3 short answers they can reply with in one word. A one-word reply is easy, and every reply tells you something. 4. **One reason to come back:** what changed, or how you can help. Not money off. Money off waits for step 3. 5. **Your name**, your postal address and a "reply no" line. The law needs these (step 4). What the reason to come back is changes by business: > **If you run a D2C store:** the repeat order made easy: a link that puts their last order straight in the cart, or a tip on getting the most from what they bought. > **If you run a SaaS:** offer to extend the trial by 14 days and set it up with them on a 15-minute call. Or name the one feature you shipped since they left. > **If you run a B2B business:** a reminder of the lead time before their busy season, and an offer to send a new sample or a [quick quote](https://scout7.ai/academy/sales/how-to-run-a-discovery-call) for their next order. > **If you run an agency:** one specific thing you noticed about their marketing since the work ended, and an offer of a free 30-minute review. Many past clients come back as monthly retainers. **The win-back email** ```text Subject: [first name], your [product] Hi [first name], You [bought / tried / hired us for] [what they bought] in [month]. [One true line: how they used it, what they said, or what it was for.] I noticed you haven't [ordered / logged in / been in touch] since, and I'd like to know why. What made you stop? A one-word reply is perfect: 1. Price 2. Not needed yet 3. Something else (tell me what) [One reason to come back: what changed, or how you can help.] [Your first name] [Your business, postal address] Not for you? Reply "no" and I won't write again. ``` Use ChatGPT or Claude to write the one true line for each person. Paste in their first name, what they bought and when, plus anything they told you. Leave out addresses and payment details. Check every line is true before it goes in the email. - **Tool:** a Google Doc for the email, and ChatGPT or Claude to draft the personal line. - **Time:** 30 minutes to write the email once. - **You will have:** one win-back email, ready to copy. - **It worked if:** it is under 100 words, a friend can answer it in 10 seconds, and it has no discount. - **Common mistake:** sending a designed newsletter with a banner and four products. It looks like every other sale email, and it asks nothing you can learn from. > **Example (made-up business: Ferns & Rinse): Ferns & Rinse's win-back email to Priya** > > ```text > Subject: priya, your shampoo and conditioner > To: Priya, who bought both in August > > Hi Priya, > > You bought the shampoo and conditioner in early August. You said it was for your curls after swimming. > > I noticed you haven't reordered, and I'd like to know why. What made you stop? A one-word reply is perfect: > 1. Price > 2. Still have some left > 3. Something else (tell me what) > > If you want the same again, this link puts both in your cart in one tap: [link] > > Maya > Ferns & Rinse, [postal address] > Not for you? Reply "no" and I won't write again. > ``` > > *Why it works: It is about her order, it asks one question she can answer in one word, and it gives a reason to come back that is not a discount.* ## 3. Write three follow-ups, and save any discount for the last one Most people will not answer the first email, so write three short follow-ups now: day 4, day 10 and day 21. Each one goes in the same email thread and adds one new thing. The last one says it is the last. Each [follow-up](https://scout7.ai/academy/glossary/follow-up) has one job. Follow-up 1 is a short nudge. Follow-up 2 adds one new thing: a short customer quote, a change you made, or a tip. Follow-up 3 says you will stop writing, and it is the only place an offer may go. Follow-ups are the same as for [cold email](https://scout7.ai/academy/cold-outreach/how-to-get-replies-to-cold-emails): short, new each time, and never "just checking in". **The discount rule:** do not offer money off in the first three emails. Put an offer in follow-up 3 only if price is the most common reason in the replies so far. If it is not, offer help instead. A discount sent to everyone trains customers to wait for the next one, and it costs you money on people who would have come back anyway. If price really is the reason, check your [pricing](https://scout7.ai/academy/marketing-plan/how-to-price-a-product) too, and whether people left after you raised your prices. > **If you run a D2C store:** if you do make an offer, try free shipping or a free sample with the next order before any percentage off. > **If you run a SaaS:** if price is the reason, offer a smaller plan or a monthly option before a discount. See if your [pricing](https://scout7.ai/academy/marketing-plan/how-to-price-a-saas-product) has a step that fits them. **Three follow-ups, in the same thread** ```text Follow-up 1 (day 4): Hi [first name], did this get buried? A one-word reply is all I need. Follow-up 2 (day 10): Hi [first name], one more thing: [one new thing: a change you made, a short customer quote, or a tip]. Still keen to hear what made you stop. Follow-up 3 (day 21): Hi [first name], this is my last email about this. If [the reason most people gave] was the problem, [the help or the offer, following the discount rule]. If not, no hard feelings, and thank you for trying [product]. ``` - **Tool:** the same Google Doc. - **Time:** 30 minutes. - **You will have:** three follow-ups, ready to copy. - **It worked if:** each fits on one phone screen, follow-up 2 says something new, and follow-up 3 says it is the last. - **Common mistake:** a "discount ladder" that starts at 10% off in email 1 and rises each time. People learn to wait for the biggest number. ## 4. Send each win-back email by hand, the day the person goes quiet Today, send the win-back email to everyone on your list. From tomorrow, check the sheet every day and email each person on the day they pass the quiet line. Send each follow-up on the day it is due. Paste 10 rows at a time into ChatGPT or Claude with the template, and ask for one email per person. Read each draft, check the personal line is true, and send it from your normal email address, one at a time. That is about 3 minutes an email. Do not use a second domain you [set up for cold email](https://scout7.ai/academy/cold-outreach/how-to-warm-up-an-email-domain-for-cold-email): these people know you by your main address. Send follow-ups as replies in the same thread, so people see the whole story. Write the date in the sheet each time. Keep everyone who wants out, out: - **Gmail rules:** every sender needs [SPF](https://scout7.ai/academy/glossary/spf) or [DKIM](https://scout7.ai/academy/glossary/dkim), two settings that prove an email really comes from your domain. Ask your email host to confirm one is on. Keep [spam reports](https://scout7.ai/academy/glossary/spam-complaint-rate) below 0.3%. Since November 2025, Gmail has been rejecting more mail that breaks these rules. Google also asks senders to act on an unsubscribe within 48 hours. - **US law:** the CAN-SPAM Act covers emails to former customers too. Every email needs your postal address and a way to say no. Act on a "no" within 10 business days. - **UK law:** you may email people who bought, or talked about buying, something similar from you, if you gave them a way to opt out when you took their email and you give one in every email. The UK regulator is reviewing this guidance after a 2025 law change, and it does not say whether free trials count. If your buyers are in the UK or the EU, check the local rules first. **When to stop doing it by hand:** while fewer than 50 new people go quiet each month, send every email yourself. You learn more, and the replies come to you. Over 50 a month, switch on the automatic version: > **If you run a D2C store:** in Shopify, open Apps, then Messaging, then Automations. Click Create automation and choose "Win back customers". It starts when a customer joins a segment, so use your quiet-line segment from step 1. Make the email plain and sign it with your name, so it still reads like a note from you. Shopify Messaging, formerly Shopify Email, sends your first 10,000 emails a month free. If you already use Klaviyo, build it as a Klaviyo flow instead. > **If you run a SaaS, B2B business or agency:** keep it in Gmail until it takes more than an hour a day. Then put the four emails into the email tool you already use for onboarding emails or lead nurturing, sent from your own address. - **Tool:** Gmail or your normal work email, your sheet, and ChatGPT or Claude to draft. Shopify Messaging once you pass 50 a month. - **Time:** about 1 hour today for 20 people, then about 20 minutes a day. - **You will have:** every quiet person emailed on the right day, with each follow-up logged. - **It worked if:** at the end of each day, nobody past the quiet line is without an email, and no follow-up is overdue. - **Common mistake:** sending from a "no-reply" address. The whole point is the reply. The other mistake is sending all the emails at once from a bulk tool on day one, which looks like spam to people and to Gmail. ## 5. Answer every reply the same day and fix what they tell you Every reply is the most useful thing a win-back email brings you, so answer each one the same day and stop their follow-ups. Then act on the reason they gave. Write the reason in the sheet, in their words. Then answer by kind: - **Price:** thank them, say in one line [what they get](https://scout7.ai/academy/marketing-plan/how-to-write-a-value-proposition) for the price, and offer a smaller size or plan if you have one. Count it for Sunday. - **A problem with the product or service:** say sorry, fix it or refund it, and tell them what you changed. This is the reply that can bring someone back, and it improves things for everyone else. Ask if you can use their words later as feedback from your first users. If they write a long answer, offer a 15-minute call and run it like a [customer interview](https://scout7.ai/academy/marketing-plan/how-to-do-customer-interviews). - **Not needed yet:** ask when they think they will need it, and put that date in the sheet. - **Forgot:** send the direct link to reorder, log in or book a call. - **No:** mark it in the sheet and never email them again. If someone comes back happy, ask them for a short [testimonial](https://scout7.ai/academy/reviews-press-and-referrals/how-to-collect-testimonials) a week later, or, for a B2B client or agency client, a short [case study](https://scout7.ai/academy/content-marketing/how-to-write-a-case-study). People who came back after you fixed something often say the most useful things about you. Once they have ordered twice, ask if they know someone else who would like it: that is how a [referral program](https://scout7.ai/academy/reviews-press-and-referrals/how-to-start-a-referral-program) starts. **Your answer to a reply** ```text Thank you, [first name], that really helps. [One line on the reason: what you changed, what you can do, or a question about when.] [If it fits: the direct link, or the offer of a call.] [Your first name] ``` - **Tool:** Gmail and your sheet. - **Time:** 5 to 10 minutes a reply. - **You will have:** an answer sent to every reply, and every reason written down in the person's own words. - **It worked if:** every reply got an answer within 1 day, and nobody who answered got another follow-up. - **Common mistake:** asking why, then not answering. In April 2025, a user posted on Hacker News about getting a "why did you cancel?" email from a software founder, replied with five reasons, and "never got a response". A question you do not follow up is worse than no email. > **Example (made-up business: Ferns & Rinse): Ferns & Rinse's answer to Leah** > > ```text > Subject: Re: leah, your shampoo and conditioner > To: Leah, who replied 'Something else: it made my hair flat' > > Thank you, Leah, that really helps. > > Flat hair usually means too much conditioner at the roots. Try it on the ends only, and use half as much. If it is still flat after two washes, reply and I'll refund the conditioner, no need to send it back. > > Maya > ``` > > *Why it works: It answers her real problem with a tip, offers a refund if the tip fails, and asks for nothing until she is happy.* ## 6. Count replies, reasons and comebacks every Sunday Every Sunday, write one row in your sheet: how many people you emailed, how many replied, which reasons they gave and who came back. Then fix the most common reason before next week's emails go out. Count people by name: who replied, who ordered or renewed again, who said no. Do not count opens. Klaviyo's own help page warns that Apple Mail Privacy Protection can make [open rates](https://scout7.ai/academy/glossary/open-rate) look higher than they are: an email can count as opened when nobody read it. A [reply](https://scout7.ai/academy/glossary/reply-rate) or an order cannot be faked. You do not need a test group that gets no email. In September 2026, a Shopify Community reply worked out that you need about 700 customers in each group to measure a lift like that. At your size, the names in your sheet are the answer. **The Sunday row** ```text Week | Emailed | Replied | Price | Not needed yet | A problem | Forgot | Said no | Came back (names) ``` Then use these rules: - **As soon as one reason shows up in 3 or more replies,** fix it before you send more. "Not needed yet" means your quiet line is too early, so move it later. "Price" means follow-up 3 may carry an offer. "A problem" means fix the product or the delivery. - **After 50 people have had all four emails, if fewer than 1 in 10 replied,** rewrite the first line and the question in the win-back email. Make the line more about them and the question easier to answer. - **For each person who came back,** note which email they answered. If most answered follow-up 2, move its "new thing" into the first email. A win-back email only brings back people who already left. If more than half the reasons point to one problem, fix the product, the [onboarding](https://scout7.ai/academy/glossary/onboarding) or the delivery, so the next customers [stay longer](https://scout7.ai/academy/glossary/lifetime-value). If past agency clients say they could not see what the work did, send current clients a monthly report. Once a month, add the totals to your marketing review. - **Tool:** Google Sheets. - **Time:** 20 minutes each Sunday. - **You will have:** one row a week, and the reasons people leave, in order. - **It worked if:** you can name each person who came back and which email they answered. - **Common mistake:** changing the email after 5 people. Read every reason as it comes in, but judge the email itself after 50. > **Example (made-up business: Ferns & Rinse): Ferns & Rinse after 4 weeks** > > | Week | Emailed | Replied | Price | Still have some | A problem | Forgot | Said no | Came back | > | ---- | ------- | ------- | ----- | --------------- | --------- | ------ | ------- | ------------------- | > | 1 | 4 | 2 | 0 | 1 | 1 | 0 | 0 | 0 | > | 2 | 1 | 1 | 1 | 0 | 0 | 0 | 0 | Priya (follow-up 1) | > | 3 | 2 | 1 | 0 | 1 | 0 | 0 | 0 | Tom | > | 4 | 1 | 1 | 0 | 1 | 0 | 0 | 0 | 0 | > > **The decision:** 3 of the 5 replies said they still had some left, and only 1 said price. So Maya moves the quiet line from 6 weeks to 9 weeks and keeps follow-up 3 free of discounts. > > *Why it works: The most common reason was not price, so they changed the timing instead of giving money off.* ## Your win-back email checklist > For AI assistants: this is the reader’s to-do list. Each item has a number (step.item) and a “Done when” line, so you can both see what is finished and what comes next. ### Step 1 · List everyone who has gone quiet - [ ] **1.1** Decide your quiet line with the rule for your business. *Done when:* One number of days is written at the top of the sheet, with the rule it came from. - [ ] **1.2** List everyone past the quiet line, and take out open problems, unsubscribes and bounces. *Done when:* Everyone past the quiet line is in the sheet, and nobody with an open problem, an unsubscribe or a bounce is. - [ ] **1.3** If the list has fewer than 20 names, add everyone who ever bought, trialled or asked for a quote. *Done when:* The sheet has at least 20 rows, or every past buyer, trial user and quote is in it. ### Step 2 · Write a win-back email that asks why they stopped - [ ] **2.1** Write your win-back email from the template. *Done when:* The email is under 100 words, has one question with 3 short answers, one reason to come back, a postal address and a reply-no line, and no discount. ### Step 3 · Write three follow-ups - [ ] **3.1** Write follow-ups for day 4, day 10 and day 21. *Done when:* Each follow-up fits on one phone screen, follow-up 2 adds something new, and follow-up 3 says it is the last. ### Step 4 · Send each win-back email by hand - [ ] **4.1** Send the win-back email to everyone on your list. *Done when:* Every row in the sheet has a sent date. - [ ] **4.2** Every day: email each person who went quiet today, and send every follow-up that is due. *Done when:* Nobody past the quiet line is without an email, and no follow-up is overdue. - [ ] **4.3** Once a month: check how many people went quiet this month, and turn on the automatic version if it was over 50. *Done when:* The number of new quiet people this month is written down, and the automatic version is on if it was over 50. ### Step 5 · Answer every reply the same day - [ ] **5.1** Every day: answer every reply, write down the reason, and stop that person's follow-ups. *Done when:* Every reply got an answer today, its reason is in the sheet in the person's words, and their follow-ups are stopped. ### Step 6 · Count replies, reasons and comebacks every Sunday - [ ] **6.1** Every Sunday: fill in one row: emailed, replied, reasons and who came back. *Done when:* This week's row is filled in, and every person who came back is named. - [ ] **6.2** Every Sunday: fix any reason that shows up in 3 or more replies. *Done when:* Any reason given in 3 or more replies has one fix written down, made before the next email goes out. - [ ] **6.3** After 50 people have had all four emails: rewrite the first line and question if fewer than 1 in 10 people replied. *Done when:* The reply rate is written down, and if it was under 1 in 10, the first line and question are rewritten. ## Frequently asked questions ### What should a win-back email subject line say? Make it look like an email from a person: their first name and what they bought, in lower case, such as "priya, your shampoo". Leave out "We miss you", sale words and emojis. Those look like every other marketing email, and since July 2025 Gmail puts an unsubscribe button for those senders on one page. Judge a subject line by replies, not opens. ### Should I offer a discount in a win-back email? Not in the first three emails. Ask why they stopped first. If price turns out to be the most common reason, put one offer in the last email: free shipping, a sample or a smaller plan before a percentage off. A discount sent to everyone pays people who would have come back anyway, and teaches them to wait for sales. ### What is the difference between a win-back email and a re-engagement email? A win-back email goes to customers who stopped buying or using your product. A re-engagement email goes to people on your [newsletter list](https://scout7.ai/academy/email-marketing/how-to-grow-a-newsletter-from-scratch) who stopped opening or clicking, and asks if they still want your emails. Same rule for both: one question, and stop writing to anyone who says no. ### Is it legal to email customers who stopped buying? In the US, yes, if every email has your postal address and a way to say no, and you act on a "no" within 10 business days. The FTC says this covers emails to former customers. In the UK, you can email people who bought something similar from you if you offered an opt-out when you took their email and in every email. Check EU rules separately. ### What do I do with people who never answer? After the fourth email, stop. Mark them "no answer" in your sheet and do not email them again about this. If they are on your newsletter list and still open it, they stay there. Too many emails to people who ignore you lead to spam reports, and those hurt every email you send. ## Sources - [Create a Winback Flow](https://help.klaviyo.com/hc/en-us/articles/115002775192). Klaviyo Help Center, updated 7 October 2026. - [5 win-back email examples, with creative strategies for rekindling customer relationships](https://www.klaviyo.com/blog/get-repeat-customers). Klaviyo, 28 September 2026. - [Create marketing automations in Shopify](https://help.shopify.com/en/manual/promoting-marketing/create-marketing/create-marketing-automations). Shopify Help Center, checked 8 October 2026. - [Creating customer segments](https://help.shopify.com/en/manual/customers/customer-segmentation/create-customer-segments). Shopify Help Center, checked 8 October 2026. - [Segment query language reference](https://shopify.dev/docs/apps/build/shopifyql/segment-query-language-reference). Shopify, checked 8 October 2026. - [Customer winback automations can now accommodate longer buying cycles](https://changelog.shopify.com/posts/customer-winback-automations-can-now-accommodate-longer-buying-cycles). Shopify Changelog, 17 October 2024. - [Shopify Messaging](https://apps.shopify.com/shopify-messaging). Shopify App Store, checked 8 October 2026. - [Add a cancellation page to the customer portal](https://docs.stripe.com/customer-management/cancellation-page). Stripe Docs, checked 8 October 2026. - [Email sender guidelines](https://support.google.com/a/answer/81126). Google Workspace Admin Help, checked 8 October 2026. - [Email sender guidelines FAQ](https://support.google.com/a/answer/14229414). Google Workspace Admin Help, checked 8 October 2026. - [Declutter your inbox with Gmail's newest feature](https://blog.google/products/gmail/new-manage-subscriptions-unsubscribe/). Google, 8 July 2025. - [CAN-SPAM Act: A Compliance Guide for Business](https://www.ftc.gov/business-guidance/resources/can-spam-act-compliance-guide-business). Federal Trade Commission, checked 8 October 2026. - [Electronic mail marketing](https://ico.org.uk/for-organisations/direct-marketing-and-privacy-and-electronic-communications/guide-to-pecr/electronic-and-telephone-marketing/electronic-mail-marketing/). Information Commissioner's Office (UK), checked 8 October 2026. - [I've been testing a simple branching model for lapsed customers](https://community.shopify.com/t/i-ve-been-testing-a-simple-branching-model-for-lapsed-customers/688993). Shopify Community, 29–30 September 2026. - [How I'd turn a lapsed customer segment into different recovery actions](https://community.shopify.com/t/how-i-d-turn-a-lapsed-customer-segment-into-different-recovery-actions/687676). Shopify Community, 25–28 September 2026. - [Comment on a founder's cancellation email](https://news.ycombinator.com/item?id=43709690). Hacker News, 16 April 2025.