# Trial-to-paid emails: what to send during a free trial, based on usage

> How to write free trial conversion emails from what each trial user did: which signals to watch, when the trial ending email goes out, and examples.

Source: https://behavly.io/guides/trial-to-paid-emails · Updated October 10, 2026

Trial-to-paid emails are the messages you send during a free trial to get each person to the point where your product has proven itself, and then ask them to pay at that moment, with the timing set by what they did in the trial rather than by how many days are left. Most teams send one of these: the “your trial ends in 3 days” email, identical for everyone. It’s the least informed email in the whole lifecycle. The person who used your product every day and the person who never came back after signup get the same words, and by the last few days most people have already made up their minds. The ending email collects a decision. The emails before it are where the decision gets made.

#### Split trial users by behavior, not by days left

On any given day of a trial, your users fall into a handful of groups that need opposite emails. Sort them by what they did, and the countdown becomes one input instead of the whole plan.

- **Activated**: They reached the point where the product works for them: the first invoice paid, the first report shared. They need a reason to pay now and an easy way to do it, not more education.
- **Active, not activated**: They log in and click around but haven’t got there. Selling to them is premature. Help them finish, and consider giving them more time.
- **Evaluating the price**: They’ve visited pricing or billing settings more than once, or compared plans. They have a specific question (which plan, how much for their team, who signs off) and the email should answer it.
- **Gone quiet**: One or two sessions in the first days, then nothing. An upgrade pitch reads as tone-deaf. One short note asking what they came to do is the most you should send.

#### Which trial behaviors to watch

| Signal during the trial | What it usually means | What to send |
| --- | --- | --- |
| Reached your activation event | The product has worked for them at least once | An email about what they built, and what keeps working when they pay |
| Hit a plan limit, or tried a feature outside their trial plan | Their actual workflow needs a paid plan | Name the limit and the plan that removes it, with their work saved |
| Visited pricing or billing two or more times | Comparing plans, or building a case for whoever pays | Help them choose: which plan fits how they already use it |
| Invited teammates | Becoming a team tool; the buyer may be someone else | Pricing for their seat count, plus something to forward to whoever approves spend |
| Logged in this week, no activation | Interested, but stuck | One step to value, and an offer of more time if they need it |
| No login since the first days | Not using it | One short question about what they wanted to do; no pitch |

Activation and limits are the two best moments to ask for payment, because the person has just seen, in their own work, what they’d be paying for. Both can happen on day two or on day thirteen, which is why a calendar alone can’t time this email. The pricing-page visit is the third signal worth acting on quickly; [pricing page follow-up](https://behavly.io/guides/pricing-page-follow-up) covers it in depth.

#### When to send trial emails

Here is a schedule for a 14-day trial with no card required. Shift the days in proportion for a longer or shorter trial, and keep the triggers as they are.

1. **Days 0–3: onboarding only.** Get them to activation, with no pricing in these emails. A good [onboarding sequence](https://behavly.io/guides/saas-onboarding-email-sequence) is the first half of trial-to-paid.
2. **At activation, whenever it happens: the value email.** What they just accomplished, what a paid plan keeps or adds, and the date the trial ends. This is the earliest moment an upgrade ask makes sense.
3. **At a limit, immediately.** The work they were doing is waiting on the upgrade, so the email should arrive while they’re still in the middle of it.
4. **Around the midpoint: a check by group.** Activated users need nothing yet. Active but stuck users get help with the step they’re on. Quiet users get the one short question.
5. **Three days before the end: the ending email, written per group.** Three days gives someone time to get a manager’s approval or a company card. One day doesn’t.
6. **On the last day: a short reminder.** For activated users, what happens to their work tomorrow. For active users who haven’t activated, an offer of more time.
7. **A few days after it ends: one email** to people who were active but didn’t convert, saying what’s still saved and how to pick up again. After that, they belong in your [win-back emails](https://behavly.io/guides/win-back-inactive-users).

##### If you take a card up front

With an opt-out trial, the ending email is a charge notice first. Send it a few days before the first charge, with the date, the amount and how to cancel in plain words near the top. It prevents disputes and surprised customers, and in some places a reminder like this is a legal requirement, so check the rules where you sell. The behavior-based emails above still apply; they just aren’t the ones that carry the charge date.

#### Example trial-to-paid emails

These are for Fernhill, a made-up invoicing app for freelancers. The trial lasts 14 days on the Solo plan, and activation is the first invoice paid through Fernhill.

Activated: first invoice paid on day four

> Subject: Acme paid your first Fernhill invoice
>
> Hi Jonas,
> 
> Acme paid the invoice you sent through Fernhill on Tuesday, straight into your account, without you writing a single reminder.
> 
> On a paid plan, Fernhill keeps doing that for every client: it sends the polite nudge when an invoice is late and marks it paid when the money lands. Your trial runs until the 18th, and your clients and invoices stay exactly as they are when you switch.
> 
> Choose a plan: [link]
> 
> Ruth

Started a recurring invoice, which is a Pro feature

> Subject: Your recurring invoice for Brightwell is saved
>
> Hi Amara,
> 
> You set up a monthly invoice for Brightwell Studio today. Your trial is on Solo, which sends one-off invoices, so Fernhill saved it as a draft.
> 
> On Pro, it goes out on the 1st of every month and follows up on its own if it’s late. The draft is kept, so it starts the moment you switch, with nothing to set up twice.
> 
> Switch to Pro: [link]
> 
> Ruth

Two people in the workspace, pricing visited three times

> Subject: Which Fernhill plan fits you and Dani
>
> Hi Leo,
> 
> You and Dani have sent 11 invoices from your shared workspace this month. That’s what the Team plan is for: you each keep your own login, and every invoice carries the studio’s name, whoever sends it.
> 
> If someone else signs off on software, here’s a one-page summary of the plan and the price for two seats, ready to forward.
> 
> Get the summary: [link]
> 
> Ruth

Trial ends in three days, no invoice sent yet

> Subject: Your Fernhill trial: three days left
>
> Hi Sofia,
> 
> You’ve added your business details and two clients, so the only step left before your first invoice is choosing what to bill.
> 
> If the trial is running out before you have real work to invoice, I can add 14 days. No card needed, and everything you’ve set up stays where it is.
> 
> Add 14 days: [link]
> 
> Ruth

Trial ended, was active, didn’t upgrade

> Subject: Your Fernhill invoices are still here
>
> Hi Ben,
> 
> Your trial ended on Sunday. The six invoices and four clients you set up are saved, and your two unpaid invoices still link to their payment pages, so those clients can pay as usual.
> 
> When you choose a plan, you start exactly where you left off, including the reminder schedule you set for Northgate.
> 
> Pick up where you left off: [link]
> 
> Ruth

#### Trial-to-paid mistakes to avoid

- **One countdown for everyone.** The daily user and the person who never came back need different emails. The days-left number can go in all of them; the rest shouldn’t be shared.
- **Asking before value.** A pricing email on day one asks for money before the product has done anything. Ask at activation or at a limit, when the person has a reason to say yes.
- **Discounts by default.** A discount sent to every trial user also goes to the ones who were going to pay anyway, and teaches the rest to wait for one. If you discount, do it for a reason, like a move to annual billing.
- **Threats about data.** “Your account will be deleted” is a pressure tactic. Say plainly what happens to their work when the trial ends, and for how long you keep it.
- **Forgetting who pays.** In team trials, the person using the product often isn’t the one with the card. Give them something to forward: the plan, the price for their seat count, and what the team has already built.
- **Treating “can I have more time?” as a lost sale.** It’s a buying signal from someone who wants to keep going. Say yes quickly to people who were active.
- **Stopping at expiry.** An active trial user who didn’t convert is still one of your warmest leads the day after the trial ends.

#### How to run this in Behavly

Behavly tracks what each signed-in user does in your product, runs the path you describe, and writes every email from that person’s activity, so the activated user and the stuck one get different emails from the same path.

1. **Install the tracking snippet** from **User Activity → Setup** on your signed-in pages, and send the actions that matter with `behavly.track`: your activation event (say `invoice_paid`) and the upgrade itself (`upgraded`). The snippet recognizes the signed-in session, so there’s no identify call to wire up.
2. **Connect your mailbox** in **Settings → Email**. Emails go out over IMAP/SMTP from your own address, so a trial user can reply to a person.
3. **Start from the Trial ending example.** In **Campaigns → New Campaign**, choose **Behavly-Agent campaign**, then **Use an example** and pick **Trial ending**. Or describe your trial path in words at the top of **Blocks** and choose **Build it**.
4. **Make the upgrade the goal.** Under **Goal**, pick your `upgraded` event and turn on **They reach the goal** under **Leave the path when**. Behavly counts who upgrades and credits the last email each person got before they did, including upgrades up to 7 days after their last email.
5. **Branch on what they did.** **Branch** on **did an action in your product** for activation, on **visited a page** (**Starts with** `/pricing`) for price questions, and on **logged in to your site** to separate the active from the quiet. Waits count from the previous step, so where an email has to land on a particular trial day, use **Wait for a set time** and check that the waits add up to your trial length.
6. **Test the ending email.** **A/B test** on that step tries a second set of instructions on half the people who reach it. Behavly judges the two versions on the goal and names a winner only once each has at least 30 sends.
7. **Read before it sends.** **Preview** any step for a real trial user, or **Send the path to me** to get the whole path in your inbox. Turn on **Hold Behavly-written emails for approval** and you approve the emails before they go out.

Replies land in the **Inbox** with each person’s activity attached and a status Behavly picks from what they wrote, such as **High-intent** or **Follow up**. With **Draft a reply when they’re interested or ask something** turned on, a suggested answer to “can I get more time?” is already waiting there for you to check and send.

_The Sender step. The voice you pick shapes how each email is written, not just the From line._

## Questions

### When should I send the trial ending email?

Three days before the trial ends, so someone who needs a manager’s approval or a company card has time to get it, plus a short reminder on the last day. If you charge automatically, include the charge date and the amount.

### Should I offer a discount to convert trial users?

Not by default. A discount sent to everyone also reaches people who were going to pay anyway; for active users who simply ran out of time, extra trial days solve the actual problem.

### Should I extend a free trial when someone asks?

For people who used the product but didn’t reach the point where it pays off, yes, and quickly. For people who never came back after the first day, more time doesn’t address why they left.

### Do trial emails change if I require a card up front?

Yes. With a card on file, the ending email is a charge notice and has to state the date, the amount and how to cancel. Without one, it’s a decision prompt, so lead with what they’ve built and what keeps working when they pay.

## Related

- [SaaS onboarding email sequence: what to send, based on what users actually do](https://behavly.io/guides/saas-onboarding-email-sequence)
- [How to follow up with users who visited your pricing page](https://behavly.io/guides/pricing-page-follow-up)
- [Win-back emails for inactive SaaS users](https://behavly.io/guides/win-back-inactive-users)
- [Behavly Agent Campaigns](https://behavly.io/help-center/campaigns/behavly-agents)