The Best Time to Send a ‘Winback’ Email (Backed by Data from 50+ eCommerce Brands)
If you are not sending winback emails at the right time, you are leaving serious revenue on the table.
At Milhook, we have worked with over 50 eCommerce brands and studied hundreds of email flows to uncover when customers are most likely to return and when your winback emails are just wasting inbox space.
In this guide, we will break down:
What a winback email is and why it works
The data-driven sweet spot for timing
Segmenting winback campaigns for better results
Real examples from top-performing brands
Pro tips to boost engagement and conversions
Let’s dive in.
What Is a Winback Email?
A winback email is a message sent to re-engage inactive or lapsed customers—those who have not purchased or interacted with your brand in a set period of time. These emails are critical for retaining more customers without spending more on acquisition.
Why Winback Emails Matter
It costs five times more to acquire a new customer than to retain an existing one
The probability of selling to an existing customer is 60 to 70 percent, compared to 5 to 20 percent for a new prospect
Winback emails drive direct revenue, improve list hygiene, and increase customer lifetime value (CLTV)
The Best Time to Send a Winback Email (Based on Real Data)
After analyzing customer behavior across more than 50 eCommerce brands, including DTC apparel, outdoor gear, and pet product businesses, we found a clear trend:
The optimal time to send your first winback email is between 45 and 60 days after a customer’s last purchase.
Why 45 to 60 Days Works Best
Sending too early, before 30 days, feels unnecessary. Customers do not feel "gone" yet
Sending too late, after 90 days, results in lower engagement and minimal conversion
45 to 60 days strikes the ideal balance. Your brand is still familiar, and the timing allows for urgency to take hold
How to Segment for Better Winback Timing
Not all customers behave the same way. The most effective winback strategies use behavioral segmentation to tailor both timing and messaging. Here are a few proven ways to segment:
1. One-Time Buyers vs. Repeat Buyers
One-time buyers should receive a winback email around 45 days after their last purchase. They are at the highest risk of never returning
Repeat buyers may benefit from a delay to 60 or even 75 days. They have a stronger connection to the brand and may not need immediate re-engagement
2. High-AOV vs. Low-AOV Customers
High average order value (AOV) customers may require a longer time window between 60 and 90 days, combined with a more exclusive offer
Low-AOV customers tend to respond better to value-driven reminders sent around 30 to 45 days after their last purchase
3. Product Type and Rebuy Cycle
A skincare brand may see better results by sending winback emails around 30 days due to product usage cycles
A furniture or seasonal gear brand might delay winback campaigns to 90 days or longer
Actionable Tip: Use your email platform’s automation tools to create dynamic winback triggers based on past order behavior, AOV, and frequency
High-Converting Winback Email Examples
Here are three examples of real winback emails that performed well for Milhook clients:
Subject Line: Still thinking about us?
Timing: 45 days after last purchase
Why it worked: Soft tone and no pressure. It acts as a gentle nudge rather than a sales pitch
Subject Line: Here’s 15 percent off to come back today
Timing: 60 days
Why it worked: The incentive is introduced at the right time, when most customers are starting to drift
Subject Line: We miss you and your inbox
Timing: 75 days
Why it worked: Emotional connection and reminder of brand value. Works especially well with lifestyle and fashion brands
Pro Tips to Make Your Winback Emails Perform Even Better
Use Personalized Recommendations
Include dynamic content such as products they previously viewed, or categories related to past purchases
Offer Tiered Incentives
Instead of giving a discount right away, escalate the value of each follow-up email:
Email 1 (45 days): Reminder email with no offer
Email 2 (60 days): Introduce a small incentive, like 10 percent off
Email 3 (75 days): Final reminder with a stronger offer or limited-time promo
Clean Your List
If a customer does not open or engage with three winback emails, consider suppressing them or adding them to a re-permission campaign to protect your sender reputation
A/B Test Your Timing
Every audience behaves differently. Use split tests to find your ideal timeframe:
Group A: First winback at 45 days
Group B: First winback at 60 days
Compare open rates, click rates, and conversions to find what works best
Conclusion: Timing Can Make or Break Your Winback Campaign
Winback emails are one of the most effective ways to re-engage customers and recover lost revenue. But without proper timing, you risk losing their attention for good.
At Milhook, we design strategic email automations tailored to your customers’ behavior and your brand’s lifecycle. From timing to design and copy, our winback flows are built to perform.
Want us to create your winback flow from start to finish?
Explore our packages nowThe Best Time to Send a ‘Winback’ Email (Backed by Data from 50+ eCommerce Brands)
If you are not sending winback emails at the right time, you are leaving serious revenue on the table.
At Milhook, we have worked with over 50 eCommerce brands and studied hundreds of email flows to uncover when customers are most likely to return and when your winback emails are just wasting inbox space.
In this guide, we will break down:
What a winback email is and why it works
The data-driven sweet spot for timing
Segmenting winback campaigns for better results
Real examples from top-performing brands
Pro tips to boost engagement and conversions
Let’s dive in.
What Is a Winback Email?
A winback email is a message sent to re-engage inactive or lapsed customers—those who have not purchased or interacted with your brand in a set period of time. These emails are critical for retaining more customers without spending more on acquisition.
Why Winback Emails Matter
It costs five times more to acquire a new customer than to retain an existing one
The probability of selling to an existing customer is 60 to 70 percent, compared to 5 to 20 percent for a new prospect
Winback emails drive direct revenue, improve list hygiene, and increase customer lifetime value (CLTV)
The Best Time to Send a Winback Email (Based on Real Data)
After analyzing customer behavior across more than 50 eCommerce brands, including DTC apparel, outdoor gear, and pet product businesses, we found a clear trend:
The optimal time to send your first winback email is between 45 and 60 days after a customer’s last purchase.
Why 45 to 60 Days Works Best
Sending too early, before 30 days, feels unnecessary. Customers do not feel "gone" yet
Sending too late, after 90 days, results in lower engagement and minimal conversion
45 to 60 days strikes the ideal balance. Your brand is still familiar, and the timing allows for urgency to take hold
How to Segment for Better Winback Timing
Not all customers behave the same way. The most effective winback strategies use behavioral segmentation to tailor both timing and messaging. Here are a few proven ways to segment:
1. One-Time Buyers vs. Repeat Buyers
One-time buyers should receive a winback email around 45 days after their last purchase. They are at the highest risk of never returning
Repeat buyers may benefit from a delay to 60 or even 75 days. They have a stronger connection to the brand and may not need immediate re-engagement
2. High-AOV vs. Low-AOV Customers
High average order value (AOV) customers may require a longer time window between 60 and 90 days, combined with a more exclusive offer
Low-AOV customers tend to respond better to value-driven reminders sent around 30 to 45 days after their last purchase
3. Product Type and Rebuy Cycle
A skincare brand may see better results by sending winback emails around 30 days due to product usage cycles
A furniture or seasonal gear brand might delay winback campaigns to 90 days or longer
Actionable Tip: Use your email platform’s automation tools to create dynamic winback triggers based on past order behavior, AOV, and frequency
High-Converting Winback Email Examples
Here are three examples of real winback emails that performed well for Milhook clients:
Subject Line: Still thinking about us?
Timing: 45 days after last purchase
Why it worked: Soft tone and no pressure. It acts as a gentle nudge rather than a sales pitch
Subject Line: Here’s 15 percent off to come back today
Timing: 60 days
Why it worked: The incentive is introduced at the right time, when most customers are starting to drift
Subject Line: We miss you and your inbox
Timing: 75 days
Why it worked: Emotional connection and reminder of brand value. Works especially well with lifestyle and fashion brands
Pro Tips to Make Your Winback Emails Perform Even Better
Use Personalized Recommendations
Include dynamic content such as products they previously viewed, or categories related to past purchases
Offer Tiered Incentives
Instead of giving a discount right away, escalate the value of each follow-up email:
Email 1 (45 days): Reminder email with no offer
Email 2 (60 days): Introduce a small incentive, like 10 percent off
Email 3 (75 days): Final reminder with a stronger offer or limited-time promo
Clean Your List
If a customer does not open or engage with three winback emails, consider suppressing them or adding them to a re-permission campaign to protect your sender reputation
A/B Test Your Timing
Every audience behaves differently. Use split tests to find your ideal timeframe:
Group A: First winback at 45 days
Group B: First winback at 60 days
Compare open rates, click rates, and conversions to find what works best
Conclusion: Timing Can Make or Break Your Winback Campaign
Winback emails are one of the most effective ways to re-engage customers and recover lost revenue. But without proper timing, you risk losing their attention for good.
At Milhook, we design strategic email automations tailored to your customers’ behavior and your brand’s lifecycle. From timing to design and copy, our winback flows are built to perform.
Want us to create your winback flow from start to finish?
Explore our packages now
