Cold Subscriber Win-Back and List Sunset Plan
Defines your real cold segment, writes a 3-email click-to-stay win-back, and sets a deliverability-safe send and suppression plan.
Before & after
Same prompt, same agent — the only difference is the skill.
You could send a reengagement campaign to inactive subscribers. You might offer an incentive like a discount or new feature they might like. You could also ask why they're not engaged and give them an option to stay or unsubscribe. You'd probably want to segment your inactive list and tailor the message. You might use a few emails spaced out over 1-2 weeks. I'd suggest making the subject line compelling and keeping the message short. How long has it been since they opened your emails?
REENGAGEMENT EMAIL SEQUENCE (7-day interval, no spam) EMAIL 1: "We miss you" (Day 1) Subject: "One thing has changed since you left" Body: Personal angle, no pressure, pure value proposition (1 new feature or social proof story) CTA: Single link to blog post or webinar recording EMAIL 2: "Your feedback matters" (Day 8) Subject: "2 minutes: Why did you unsubscribe from us?" Body: Genuine curiosity, no sales pitch CTA: 1-click feedback survey + unsubscribe button prominent Hook: "Your answer helps us get better for others like you" EMAIL 3: "Try us again, no commitment" (Day 15) Subject: "Fresh start: 30-day free trial" Body: Acknowledge they tried you before, show what's new, frame as "summer refresh" CTA: Activation link, no credit card required Frequency: Win back works only once per 6 months per user SEGMENT Send only to: Opened > 5 emails, last open > 60 days ago NEVER send to: Never-openers, complained or marked spam EXPECT Reactivation rate: 3-7% of inactive list Unsubscribe during sequence: 5-8% (this is healthy, not waste) Stop after email 3; honor their silence
About this skill
A big slice of your list hasn't opened anything in months. You're paying for those subscribers, your open rate keeps sliding, and you're not sure whether to email them or quietly delete them. This skill makes that call for you and builds the campaign: the right segment, a short sequence that gets real readers to raise their hand, and a clean rule for everyone who doesn't.
What it does
- Defines "inactive" with clicks, replies, and purchases, because Apple Mail Privacy Protection makes opens unreliable
- Splits the cold list into tiers: who gets the sequence, who gets it last in small batches, and who gets suppressed without being emailed
- Writes a 3-email click-to-stay sequence: a value email, a choice email (including "fewer emails"), and an honest last call
- Sets a batched send plan with stop rules for spam complaints and bounces, so the cleanup doesn't damage inbox placement for your engaged readers
- Ends with a suppression rule and an ongoing monthly sunset automation, so you never need another giant cleanup
- Reviews your existing win-back drafts and flags guilt copy, fake urgency, and missing stay links
What you get
A ready-to-run plan with segment rules, three drafted emails with subject lines, a send schedule with pause thresholds, and the post-campaign suppression and measurement plan.
Best for
Newsletter writers, creators, and small e-commerce brands on Kit, Mailchimp, beehiiv, or similar platforms with a growing pile of subscribers who no longer read.
SKILL.md preview
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name: cold-subscriber-win-back-sunset
description: Builds a win-back and sunset plan for inactive email subscribers. It defines the cold segment without trusting inflated opens, tiers it by risk, writes a 3-email click-to-stay sequence, sets a batched send plan with stop rules, and decides exactly who gets suppressed. Use when the user says "a third of my list hasn't opened in months", "write a re-engagement campaign", "should I just delete my inactive subscribers", "my open rates keep dropping", "I'm paying for subscribers who never read", "my emails started going to spam", "win back cold subscribers", or "set up a sunset policy".
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# Cold Subscriber Win-Back and List Sunset Plan
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