Prompt: Write Re-engagement and Win-Back Email Copy
For Email Marketing Specialists
Level 1 — Free chatbot (ChatGPT or Claude) | Time: 5 minutes
The Prompt
Write a re-engagement email (or win-back sequence) for the following situation:
Audience: [describe who they are and how long they've been inactive]
Inactivity period: [how long since last open/purchase — e.g., "90 days no open" or "6 months no purchase"]
What they originally subscribed for / purchased: [context on their original intent]
What's changed since they last engaged: [new features, new products, improvements]
Incentive: [yes/no — if yes, describe the offer]
Goal: [re-engage or cleanly sunset (remove from list)]
Brand voice: [tone]
Write:
- Subject line (3 options — one personal/direct, one curiosity, one low-pressure)
- Preview text
- Opening line that acknowledges the gap naturally without being needy
- Body copy (120-150 words)
- CTA (should feel low-stakes — "come back," not "buy now")
- Optional: P.S. line that serves as an easy opt-out ("not interested? no hard feelings")
Avoid:
- "We've been thinking about you" (too presumptuous)
- Excessive apology ("we're sorry we haven't been in touch")
- Hard sell pressure
- Subject lines starting with "Hey" (spam filter risk)
How to Use This
Re-engagement copy is harder than promotional copy because you're asking for attention from someone who has already stopped giving it. The copy needs to:
- Acknowledge the silence without making it awkward
- Give them a genuine reason to care again (new thing, better thing, valuable offer)
- Make the re-engagement action feel small ("just check this out," not "come back and buy everything")
The opt-out P.S. line is counterintuitive but powerful: giving subscribers an easy, graceful exit actually reduces unsubscribes because it removes the pressure. People who would have unsubscribed instead just ignore the email — and you keep the contact on your list for later.
For sunset emails specifically (when you're about to remove inactive contacts): adding "we'll be removing you from our list in 7 days" typically gets 5-10% of supposedly dead contacts to open. The threat of finality is the strongest re-engagement trigger.
Example
Input:
Audience: E-commerce skincare brand, subscribers who haven't purchased in 5 months
Inactivity: 5 months no purchase (still opening occasionally)
Original: First-time buyers of moisturizer 5 months ago
What's changed: New formula, 3 new products launched, sustainability initiative
Incentive: 15% off — reveal in email body, not subject line
Goal: Win back a purchase
Brand voice: Warm, honest, not pushy. Like a friend who works in beauty.
What the opener should NOT look like: "Hey, it's been a while! We've missed you and wanted to reach out..."
What it SHOULD look like: "Five months is a long time in skincare. Since your last order, we've launched a reformulated moisturizer, added three new products, and went fully carbon-neutral. We think it's worth another look — especially with what we have for you below."
Three-Email Win-Back Sequence
For a complete win-back sequence (not just one email), use this prompt:
Write a 3-email win-back sequence for [audience] who last purchased [X months ago].
Email 1: Reconnection — no offer, just "here's what's new"
Email 2 (7 days later): Soft offer — introduce [incentive]
Email 3 (7 days after email 2): Final notice — "this offer expires" or sunset message
Maintain consistent voice across all three. Don't repeat selling points between emails.
Works with: ChatGPT (free), Claude (free)