Status: 7 November 2026. A practical guide, not legal advice. Check your local email rules before you send marketing messages.
One email is easy to miss. Your message lands on a busy day, gets buried, and the customer never knew you wrote. A second email gives those people another chance to notice you, and it lets you add a reason that the first one left out.
Beyond three, the picture changes. Someone who has ignored three friendly messages is telling you something. A fourth and fifth email tend to add little goodwill, can add opt-outs and spam complaints, and may make a small local business look desperate. Advice online varies and there is no proven standard, so treat any "perfect number" with caution. Start with three, write down the results, and only then decide whether a different length fits your business.
2. The three emails and their jobs
Each email has exactly one job. If an email tries to do two, it gets muddled, and the reader does neither.
Email 1: say hello (day 1)
Job: get in touch without asking for anything big. Mention what you can do for them, link to one easy next step, and keep it short. No discount is needed here. Some people simply forgot, and a warm nudge can be enough.
Example subject lines (write your own): "A quick hello from [business]" or "[First name], how are things?"
Email 2: give a reason (about day 8)
Job: give a concrete reason to act now. Real examples: free slots next month, a new service, a seasonal check, a small offer with an end date you will honor. This is the email where an offer belongs, if you want one. If you have nothing new to say, say less rather than invent urgency.
Example subject lines: "Free slots in [month]" or "Something new at [business]"
Email 3: close politely (about day 15 to 18)
Job: tell the person honestly that this is your last message on the subject. That is not a trick. It gives people who meant to answer a clear moment to do so, and it respects those who do not want to. If an offer ends, state the date and keep to it.
Example subject lines: "One last note from [business]" or "We will stop writing after this one"
3. How far apart should they be?
About a week is a sensible default. Shorter gaps feel pushy, and much longer ones let the first email fade from memory. If your customers normally return every few months, a gap of 7 to 10 days is still fine, because you are not reminding them of an appointment, you are re-opening a conversation. Send on a regular weekday morning and avoid the days right before and after a public holiday.
Do not start all three emails for your whole list on the same day. Work in waves of a size you can handle, so that bookings and replies do not arrive all at once and so that you can answer each one the same working day.
4. Who leaves the sequence?
Before each email, compare your send list with your replies. Remove:
- anyone who replied, even with a "not now" (answer them personally instead),
- anyone who booked or bought,
- anyone who opted out or asked you to stop, which you record the same day,
- addresses that bounced.
Only the people with no reaction receive the next email. Sending email 2 to someone who already booked is the quickest way to annoy a returning customer.
5. What to count
Keep a small table with one row per email and four columns: sent, replies, bookings (or purchases), opt-outs. After the third email, compare the rows with each other and with your own expectations. Questions worth answering:
- Did email 2 bring more bookings than email 1? Then the reason matters more than the greeting.
- Did email 3 bring anything? If not, a shorter two-email version may fit your business.
- Did opt-outs rise with each email? Then the gaps are too short or the list is too old.
Do not compare your numbers with figures from other businesses or from articles. Your list, your industry and your customers are different. The only useful benchmark is your own previous round.
6. When to stop
After email 3, stop. Mark everyone who stayed silent as "resting" and leave them alone for a long while (our kit's schedule suggests a year at the earliest). If you try again, use a new reason, not the same text. Do not move silent contacts to your regular newsletter without checking that you are allowed to. And never pretend an email is "the last one" if you plan to send another.
7. Common mistakes
- Guilt trips. "We haven't seen you in ages" makes people feel judged. Write about what you can offer now.
- Fake urgency. If a deadline is extended every time, nobody believes the next one.
- Too many asks. One link or one question per email.
- No sender details. Say who you are and give an easy way to opt out.
- Changing three things at once. If you vary subject, offer and timing together, you cannot tell what worked.
8. Check your local email rules
Rules for marketing email differ by country, and sometimes by the channel and the relationship you have with the person. Before you send, check the rules where you and your customers are located, yourself or with a professional. Our guide on how to win back lapsed customers lists the points to look at and links to the official sources.
Frequently asked questions
How many win-back emails should I send?
Three is a simple place to start: a hello, a reason, a last note. Then count the results and adjust.
How long should I wait between win-back emails?
About a week. Adjust it if your customers buy much more or much less often than that.
Should I keep emailing people who never reply?
No. Stop after the last note and let them rest for a long while (a year at the earliest is the kit's suggestion).
Do I send all three emails to everyone?
No. People who reply, book or opt out leave the sequence immediately.
Important: A practical aid, not legal advice. Check your local email rules before you send marketing messages.