An expired trial email can recover users who never fully experienced your product. These aren't lost causes—they're people who showed genuine interest by signing up. Something got in the way before they converted, but that doesn't mean the opportunity is gone. With the right approach, you can bring a meaningful percentage back to complete their evaluation and become paying customers.

The difference between a win-back sequence that works and one that annoys is timing, relevance, and knowing when to stop. Expired trial users fall into different categories with different reasons for not converting. Your messaging needs to reflect that context.

This guide covers when to reach out, what to say at each stage, how to segment your approach based on engagement level, and provides complete email templates you can adapt for your SaaS.

Why Pursue Expired Trial Users

Not everyone who doesn't convert during a trial is unqualified. Many expire for reasons that have nothing to do with your product's value.

Timing was wrong. They signed up during a busy week, planned to evaluate later, and forgot. Their intent was real, but circumstances got in the way.

They got stuck. Something in your onboarding confused them. They hit a technical issue and didn't bother reaching out. A small friction point derailed what could have been a successful evaluation.

Priorities shifted. A more urgent project demanded attention. The problem they wanted to solve got deprioritized. When things calm down, they might be ready to resume.

They needed more time. Complex products require more evaluation time than a 7 or 14-day trial allows. They ran out of days before reaching their "aha" moment.

The economics make win-back campaigns worthwhile. These leads cost you nothing additional to acquire—you already have their email and some behavioral data. Even a 5-10% recovery rate from a well-executed sequence delivers meaningful revenue.

Expired vs. Churned: Different Timing, Different Approach

Expired trial users and churned paying customers require different strategies. Understanding the distinction shapes your messaging.

Expired trial users never converted. They may have barely used your product or never logged in after signup. They haven't committed money, so they have less invested in the relationship. Your goal is to restart their evaluation.

Churned customers paid at some point. They experienced more of your product, made a financial commitment, and actively decided to leave. Your approach with them involves different re-engagement strategies.

The timing window also differs. Expired trial users are most recoverable within 30 days of expiration. After that, their memory of your product fades and their situation may have changed entirely. Churned customers can sometimes be recovered months later when their circumstances change.

This guide focuses on the expired trial window—the first 30 days after trial expiration when win-back efforts have the highest success rate.

First Email: Days 1-3 After Expiration

Your first win-back email should arrive within 1-3 days of trial expiration. The user still remembers signing up, and the context is fresh.

Goal: Acknowledge the expiration without guilt, remind them of the value, and offer a clear path back.

Subject line options:

"Your [Product] trial expired – here's what's next"
"[First Name], pick up where you left off"
"Miss anything? Your [Product] access"

Tone: Helpful, not pushy. You're reminding them of an open opportunity, not pressuring them about a missed deadline.

What to include:

Direct acknowledgment that their trial ended
Brief reminder of the core problem you solve
One specific thing they could accomplish if they returned
Clear CTA to reactivate or extend

What to avoid:

Guilt-tripping language ("We noticed you left...")
Overwhelming with features
Desperation signals ("We really want you back!")

Template:

Subject: Your [Product] trial expired – here's what's next

Hey [First Name],

Your [Product] trial ended, but your account is still here.

If you ran out of time or things got busy, I get it. When you're ready, you can [reactivate your trial / start a subscription] and pick up right where you left off.

[Button: Continue Where You Left Off]

If [Product] isn't the right fit, no hard feelings. But if timing was the issue, we're here when you're ready.

[Your Name]

Second Email: Day 7 After Expiration

If the first email didn't get a response, the second email takes a different angle. A week has passed—enough time to be helpful without being annoying.

Goal: Offer value or insight that re-engages them without repeating the first message.

Subject line options:

"Quick tip for [achieving their goal]"
"What [successful customers] figured out"
"[First Name], one thing that might help"

Strategy options:

Option A: Share a quick win. Provide a useful insight related to the problem you solve. This positions you as helpful, not salesy, and reminds them of your expertise.

Option B: Social proof. Share a brief success story from a similar customer. "Last month, [Company] used [Product] to [achieve result]" gives them a concrete vision of what's possible.

Option C: Address common blockers. If you know why trials typically stall, address it directly. "If you got stuck on [common friction point], here's the quick fix."

Template (Option A - Quick Win):

Subject: Quick tip for [goal they care about]

Hey [First Name],

Whether you decide to use [Product] or not, here's something that might help with [their problem].

[2-3 sentences of genuinely useful advice]

If you want to put this into practice, your [Product] account is still set up. Just [action to reactivate].

[Button: Get Back In]

Either way, hope this helps.

[Your Name]

Third Email: Days 14-30 After Expiration

The third email is your last serious attempt for most expired trials. Beyond 30 days, recovery rates drop significantly and you risk becoming an annoyance.

Goal: Create urgency or make a compelling final offer. This is where you might introduce an incentive.

Subject line options:

"Last chance: [Offer or extension]"
"Before we close the loop"
"[First Name], final note from me"

Incentive options (use sparingly):

Extended trial: "7 more days to evaluate properly"
Discount: "20% off your first three months"
Premium support: "Free onboarding call if you restart this week"

Important: Only offer incentives if you're willing to give them to all expired trial users. Segment-specific offers can create resentment if discovered. Also, avoid training users to expect discounts by always leading with value first.

Template:

Subject: Before we close the loop

Hey [First Name],

I wanted to reach out one more time about [Product].

I'm not sure if timing was the issue or if we weren't the right fit—both are okay. But if you wanted more time to evaluate, I can extend your trial by [7 days] so you can make a fair decision.

[Button: Extend My Trial]

If you've moved on, no need to reply. I'll stop reaching out.

But if there's something I can help with—questions, a demo, or troubleshooting something that blocked you—just let me know. I'm here.

[Your Name]

When to Stop Reaching Out

Persistence becomes annoyance when you don't know when to quit. Here's when to stop:

After three emails with no engagement: If someone hasn't opened or clicked any of your three win-back emails, more emails won't help. Move them to a long-term nurture list with monthly or quarterly touchpoints, or sunset them entirely.

After an explicit "no": If someone replies saying they're not interested, stop immediately. Thank them for the response and remove them from the sequence. Respecting "no" builds goodwill—they might reconsider later or refer others.

When they take action: Obviously, stop the win-back sequence when someone converts. But also stop if they restart a trial, even if they haven't paid yet. Move them to a different sequence focused on trial conversion.

After 30-45 days: Beyond this window, your win-back sequence should end. These users can be moved to a general marketing list for product updates and content, but aggressive win-back messaging is no longer appropriate.

Segmenting by Engagement Level

Not all expired trials are the same. Segmenting by engagement level lets you tailor your messaging.

Engagement Level	Behavior During Trial	Win-Back Approach
Never activated	Signed up but never logged in or completed key actions	Focus on removing friction; ask what went wrong
Started but stalled	Logged in a few times, began setup, didn't finish	Help them complete what they started; offer assistance
Used actively	Regular usage during trial but didn't convert	Focus on conversion blockers; maybe pricing, features, timing
Power user	Heavy usage, clearly got value, still didn't convert	Direct ask about what's holding them back; personalized offer

For never-activated users, consider a different approach entirely. They might need a re-onboarding sequence, essentially restarting the trial experience with better guidance. See our guide on re-engaging inactive users.

For power users who didn't convert, the blocker is often something specific—pricing, a missing feature, internal approval. A personal outreach asking directly is often more effective than an automated sequence.

Re-Onboarding: When Users Need a Fresh Start

Some expired trial users didn't fail to convert—they failed to start. These users need re-onboarding, not win-back messaging.

Signs a user needs re-onboarding:

Never logged in after signup
Started but didn't complete setup
Used less than 20% of trial days
Never reached your activation milestone

For these users, a simple "extend your trial" message isn't enough. They need a guided restart.

Re-onboarding approach:

Acknowledge the fresh start: "Let's try this again—the right way"
Offer structured guidance: "I'll send you a 5-day plan to get started"
Reduce the activation goal: "Just one thing: [smallest valuable action]"
Provide direct support: "Reply if you get stuck on anything"

The goal isn't just more time—it's a better experience the second time around.

Win-Back Email Sequence Templates

Here are two complete sequences you can adapt for your SaaS.

Sequence A: Standard Win-Back (3 emails)

Email 1 (Day 1)

Subject: Your [Product] trial ended – what's next?
Focus: Acknowledge expiration, offer easy reactivation
CTA: Restart trial or subscribe

Email 2 (Day 7)

Subject: One thing that might help
Focus: Provide value, share quick insight
CTA: Soft invitation to return

Email 3 (Day 21)

Subject: Last note from me
Focus: Final offer or trial extension
CTA: Accept offer or provide feedback

Sequence B: Segmented Win-Back (engagement-based)

For high-engagement expired trials:

Day	Subject	Focus
1	"Noticed you were active – what happened?"	Direct ask about conversion blocker
5	"If it's about [common objection]..."	Address specific objection
14	"Let me know what would help"	Personal offer to assist

For low-engagement expired trials:

Day	Subject	Focus
1	"Looks like things got busy"	No-pressure acknowledgment
7	"Here's the fastest way to get started"	Simplified onboarding guide
21	"Want to give it another shot?"	Trial extension offer

Measuring Win-Back Success

Track these metrics for your win-back sequence:

Recovery rate: Percentage of expired trial users who restart their trial or convert within 30 days of expiration. Aim for 5-15% depending on your product and market.

Email engagement by position: Open and click rates for each email in the sequence. Drop-off between emails indicates where you're losing people.

Conversion rate by segment: Which engagement segments recover best? This tells you where to focus personalization efforts.

Time to conversion: How long after win-back outreach do users convert? This informs optimal sequence timing.

Revenue recovered: Total revenue from win-back conversions. This justifies investment in the program and provides clear ROI.

Next Steps

A win-back sequence is one part of a complete trial conversion strategy. The goal is recovering users who slipped through, but the bigger opportunity is preventing expiration in the first place.

Set up proper trial expiration emails to catch users before they expire. Build an effective re-engagement sequence for inactive users who show warning signs during the trial.

The users who expire despite these efforts are the ones you'll win back with the strategies in this guide. Some will return. The rest will have received professional, respectful outreach that leaves the door open for the future.