Best Email Tools for Free Trial Conversion in 2026
For most SaaS teams that need trial emails to change when a user's behavior changes, Customer.io is the best starting pick. Its Essentials plan starts at $100 a month, and the 10,000-profile tier is $145 a month billed monthly. If your trial list is under 2,000 subscribers, Encharge is the cheaper option at $79 a month billed yearly on its Growth plan.
Prices below come from each vendor's public pricing page as checked on 7 October 2026. Where a vendor does not publish a price for a given list size, the tables say "pricing on request" and you should ask the vendor for a quote.
What a Free-Trial Email Program Needs From Its Tool
A trial is a short period with a known end date, so the email tool has to know more than the contact's address. It needs to know where the user is in the trial, what they have done, and whether they have already paid.
- Trial state. Trial start date, trial end date, current plan and whether the trial has been extended. Most teams take this from the billing system, not from the signup form.
- Activation events. The three to five actions that show a user has found value, such as creating a first project, inviting a teammate or connecting a data source. These usually come from product analytics or your application database.
- Suppression on conversion. When a user pays, the "your trial is ending" sequence must stop at once. This is the most common trial email mistake and the one that damages trust fastest.
- Branching. Engaged users, stuck users and dormant users should get different messages. A single linear sequence cannot serve all three well.
- Transactional sending. Receipts, failed-payment notices and trial-ending confirmations should go out through a path that is separate from marketing sends, so that a marketing unsubscribe does not stop a billing message.
- Win-back segments. Expired trials that did not convert need their own list, with a clear reason for being on it, so that they are not mixed with active trials.
Not every tool covers all six needs natively. Some send email well but depend on an outside system to tell them the trial status. Others have strong branching but expect you to build the event feed yourself. The rest of this guide shows where each tool falls on that line, and which additional tools you may need to connect billing and product data.
How the Tools Are Compared
The comparison uses the same four questions for every tool. None of them is a score.
What triggers a message?
Some tools trigger on time alone, such as "three days after signup". Others trigger on events, such as "created a project" or "trial ends in 48 hours", and some also read subscription status from a billing integration. For a trial, event and billing triggers matter more than time triggers, because a user who has already converted should never receive the reminder.
Where does the trial status come from?
A tool can receive status through its own billing connector, through a webhook from Stripe or another processor, through an API call from your application, or through a tag that someone updates by hand. Each route has a different failure mode. A webhook can be delayed or missed, and a manual tag goes stale. The page notes which route each tool expects.
How is the price calculated?
Some tools charge by contact or subscriber, some by person, some by seat, some by credits or events. A tool that is cheap at 2,000 contacts can be expensive at 50,000, and the reverse is also true. Where a vendor publishes a price for a given list size, the tables show it. Where it does not, the tables say "pricing on request".
How much setup does a trial need?
A linear welcome series can be built in an afternoon. A trial with activation branching, billing suppression and sales handoff usually takes a few weeks of engineering and copy work, regardless of the tool. The setup notes below describe what that work involves for each tool.
Free-Trial Email Tools Compared
| Tool | Best for | Starting price (plan, billing) | Key limitation |
|---|---|---|---|
| Customer.io | Trial journeys that branch on product events | Essentials from $100/mo; 10,000 profiles at $145/mo billed monthly | Cost grows with profile count, and event data must be sent in |
| Encharge | Small SaaS trial lists under 2,000 subscribers | Growth at $79/mo billed yearly (up to 2,000 subscribers); $99/mo billed monthly | HubSpot, Salesforce and transactional email need the Premium plan at $129/mo billed yearly |
| Drip | Trial lists priced by people, with workflows and onsite campaigns | $39/mo for 1–2,500 people | The listed tiers cap workflows at 50 |
| ActiveCampaign | Teams that want CRM and automation in one place | Starter at $15/mo for 1,000 contacts | Price depends on contact count; advanced segmentation sits on higher tiers |
| Userlist | B2B products where a trial is run by a team | Basic at $149/mo for up to 10,000 users | Company-level tracking is the core strength, so single-user products gain less from it |
| Loops | Simple linear trial sequences with a free start | Free for up to 4,000 sends in any rolling 30 days; paid plan at $99/mo | Few behavioral triggers; free plan shows a Loops footer |
| Kit | Creators and early products with a simple welcome series | Free up to 10,000 subscribers; Creator at $33/mo billed yearly | Visual Automations and sequences start on the Creator plan |
| Intercom | Trials that combine email with in-app messages and chat | Essential at $19 per seat/mo billed yearly | Priced per seat, so cost rises with team size, not contact count |
| HubSpot Marketing Hub | Larger teams that want CRM and sales handoff | Starter at $7/mo; Professional at $800/mo | The step from Starter to Professional is large, and setup takes time |
| Make | Connecting billing and product events to your email sender | Free for 1,000 credits/mo; Core at $9/mo billed yearly for 10k credits | An automation tool, not a sender; the free plan allows 2 active scenarios |
Each Tool for Free-Trial Conversion
Each entry covers what the tool does well for trial users, where it falls short, what it costs and where to read the current pricing.
Customer.io
Customer.io is the best pick in this guide for trials that need many branches. Its visual workflow builder lets you build a trial journey around events, so the next email depends on what the user actually did in the product. A user who has created a project but not invited anyone can get a different sequence from a user who has done neither, and the branching stays readable as you add more paths.
For trial conversion, the strengths are the event-driven triggers and the segmentation that comes with them. You can keep a user in a "trial ends in 3 days" path only while they remain unconverted, and move them out when a payment event arrives. Customer.io also supports A/B testing inside its workflows, which helps when you want to compare two upgrade offers without building two separate programs.
Where it falls short: the tool expects you to send trial and billing events into it. Your application or a connector has to report activation events, and your billing system has to report trial start, extension and conversion. That is reasonable work for an engineering team but a real cost for a small team without engineers. Pricing also grows with the number of profiles, so a large free-plan user base will push the bill up quickly. Customer.io's Essentials plan starts at $100 a month, and its profile tiers run from $145 a month at 10,000 profiles, $235 at 20,000, to $505 and up at 50,000 profiles, all billed monthly. Eligible early-stage companies that have raised under $10M can receive 12 months free through the Startup Program.
Pricing: Customer.io pricing page.
Encharge
Encharge is built around SaaS lifecycle email, and it is the most cost-effective choice here for a small trial list. Its Growth plan costs $79 a month billed yearly, or $99 a month billed monthly, for up to 2,000 subscribers. The plan includes unlimited flows and team members, which matters when several people on a growth team need to build and edit trial sequences at the same time.
For trial work, the useful pattern is a flow that starts on signup, watches for activation events and exits when the user converts. Encharge handles this without a separate suppression list, which keeps the trial logic in one place. Its free email verification is included on plans, which helps with the bounce problems that trial sign-up forms often create when people type their addresses quickly.
Where it falls short: the connections to HubSpot, Salesforce and transactional email sit on the Premium plan, at $159 a month billed monthly or $129 billed yearly for up to 2,000 subscribers. If your trial team depends on those systems, you will be choosing the higher price. Once the list grows beyond 2,000 subscribers, the price is not in the pricing record used here, so you will need to ask for a quote at that size.
Pricing: Encharge pricing page.
Drip
Drip is a practical choice when your trial list is priced by people rather than by sends, and when you want a workflow builder with conditional content in the same tool. Its lower tiers include unlimited email sends, dynamic segments, onsite campaigns and up to 50 workflows. For a trial team that needs a dozen or so branching sequences rather than dozens of them, that is usually enough.
Trial tracking with Drip is built on its integrations and on custom events. Its Stripe integration can respond to subscription changes, which covers the trial-end and conversion cases that are most important for suppression. Drip's own materials describe a heritage in ecommerce, and that shows in how easily it handles discount campaigns and urgency messaging, which some SaaS teams use near the end of a trial.
Where it falls short: the workflow count is capped on the listed tiers, so a team with many trial paths will reach the limit. Activation tracking also depends on sending custom events to Drip, which is work for the developer who owns the product. Its entry price is $39 a month for 1 to 2,500 people, and the tiers step up from there. Drip's pricing page lists a 14-day free trial with no credit card required, and no ongoing free plan.
Pricing: Drip pricing page.
ActiveCampaign
ActiveCampaign suits trial teams that keep their pipeline in a CRM and want automation next to it. Its automations can branch on contact data, engagement and deal stage, and the built-in CRM lets a sales person see the trial sequence a prospect has been through before they call. For B2B products with a sales-assisted trial, that shared history is the main reason to choose it.
Its prices start at $15 a month on Starter, $49 on Plus and $79 on Pro, and Enterprise is $145 a month, all at 1,000 contacts. Those starting prices scale with the contact count you select, so a larger trial list will cost more on the same plan. The free trial on paid plans lets you test the automation builder before you commit, but that is a trial of the product, not a free plan.
Where it falls short: the automation builder is powerful, and that power takes time to learn. Advanced segmentation sits on Pro and above, so a team on Starter will get simpler branching. Trial suppression depends on the billing integration you set up, so check how the status reaches the contact before you promise a trial user that no upgrade email will arrive after they pay.
Pricing: ActiveCampaign pricing page.
Userlist
Userlist is aimed at B2B products where a trial is run by a team rather than a single person. Its company-level view shows which accounts have active trial users, which have gone quiet and which are close to a trial end. That lets you send a trial-ending message to the admin, a different one to the team members and a summary to the economic buyer, all from one account record.
Userlist's paid plans carry the price you should compare. The Basic plan is $149 a month for up to 10,000 users, and the Professional plan adds A/B split testing, conversion goals and advanced workflow features at $349 a month for up to 10,000 users. Enterprise is priced on custom message limits.
Where it falls short: company-level tracking is its core strength, so a single-user consumer trial gets less from it. The team features assume that your product can group users into accounts, which means the data model has to be right before the sequences can be useful. If your product has no account concept yet, start with a simpler tool.
Pricing: Userlist pricing page.
Loops
Loops is the simplest tool on this page, and that is its appeal for a trial with a straight path. Its free plan covers unlimited contacts, with up to 4,000 sends in any rolling 30 days to the 1,000 newest contacts. For a new product with a single 14-day trial and a welcome-to-upgrade sequence, that may be all you need at the start.
Its paid Growing Audience plan is $99 a month, and it includes transactional sends to users who are outside your audience. That matters for trial teams because receipts and trial-ending notices can go out through the same tool. The free plan adds a Loops footer and limits sends to 10 emails per second.
Where it falls short: Loops has few behavioral triggers, so it cannot easily branch on feature adoption or engagement. Once your trial sequence depends on what users do rather than when they signed up, you will need a tool with event-driven workflows. Loops is a good first sender while the product is still small, but plan the migration early if your trial design is likely to grow.
Pricing: Loops pricing page.
Kit
Kit, formerly ConvertKit, comes from creator marketing, but it is used by some small SaaS teams for trial welcome series. The free plan covers up to 10,000 subscribers, with unlimited landing pages, forms and email broadcasts, plus audience tagging and segmentation. A tag-based trial status can work when a single person owns the trial emails and the product changes slowly.
The main limit for trial work is that Visual Automations and email sequences start on the Creator plan, at $33 a month billed yearly. The Pro plan at $66 a month billed yearly adds deliverability reporting and unlimited users. The free trial on paid plans is 14 days with no credit card required.
Where it falls short: trial status has to be pushed into the tool as tags, usually through an API or an integration. Tags go stale if the sync breaks, and a stale tag can keep a converted user in a trial sequence. Kit is best where the trial is simple, and where you accept the manual upkeep that tags require.
Pricing: Kit pricing page.
Intercom
Intercom makes sense when a trial depends on more than email. Its messaging covers in-app messages, product tours, a help center and chat in one product, and the same user record drives all of them. A trial user who gets stuck inside the product can see a tour or a chat prompt on the screen where they are stuck, and the email sequence can be paused while that happens.
Its pricing is per seat. The Essential plan is $19 a seat a month billed yearly, Advanced is $85 and Expert is $132, with usage-based charges for AI outcomes and messaging on top. The cost therefore depends on how many people in your team need access, not only on how many trial users you have. The free trial is 14 days with no credit card required.
Where it falls short: if you only need email, Intercom is more than you need, and its email sequence features are one part of a larger product. Teams that already run a help desk will get the most from it. A small team that only wants trial emails will pay for capabilities it does not use.
Pricing: Intercom pricing page.
HubSpot Marketing Hub
HubSpot Marketing Hub suits a trial program that lives inside a CRM with a sales team. Workflows can enroll contacts based on behavior and deal stage, and a trial that converts to a sales-assisted deal can hand off to a representative without moving data between systems. For products where the trial is a sales stage, that connection is the reason to choose it.
The price is a large step between plans. Starter is $7 a month and Professional is $800 a month, and Enterprise is $3,600 a month. Free Marketing Hub tools are available, but the trial sequences described on this page need a paid plan. HubSpot prices Marketing Hub per plan, with a per-seat model.
Where it falls short: setup takes time, and the reporting that shows which trial emails drive upgrades is only useful once the event data is clean. A small team without a CRM owner will spend more time configuring it than sending.
Pricing: HubSpot Marketing Hub pricing page.
Tools That Feed the Trial Sequence
Most trial programs need at least one tool that moves data between your billing system, your product and your email sender. These are not email senders, but they decide how well a trial sequence can respond to what users do.
Make
Make is a visual automation tool that can take a billing or product event and pass it to an email sender. Its free plan includes 1,000 credits a month and no time limit, with a maximum of 2 active scenarios, scenarios that run at most every 15 minutes, and a 5-minute execution limit. Core costs $9 a month billed yearly, or $10.59 billed monthly, for 10k credits a month. Use it for a small number of clear routes, such as a trial-ending event that adds a contact to a suppression list.
Pricing: Make pricing page.
Zapier
Zapier connects apps through task-based automations. Its free plan includes unlimited Zaps and two-step Zaps, but only 100 tasks a month, and every successful action step uses tasks. Professional costs $19.99 a month and adds multi-step Zaps, webhooks and premium apps. A 14-day Professional trial is available without a credit card. Zapier is convenient for one-off connections, but task counts can rise quickly once a trial program has many events.
Pricing: Zapier pricing page.
Segment (Twilio Segment)
Segment collects first-party events from your product and sends them to downstream tools, including email senders. Its pricing is custom and the page publishes no list-size prices, so you will need to ask for a quote. Segment mentions a free trial for its Connections plans. It fits teams that already need a single event pipeline for analytics, email and ads.
Pricing: Segment pricing page.
Amplitude and Mixpanel
Both are product analytics tools that define the activation events used in trial sequences. Amplitude's free plan includes 2M events a month with no time limit. Mixpanel's free plan includes up to 1M monthly events, and its Growth plan is $120 a month billed yearly, or $140 billed monthly, with the first 1M events free and up to 20M monthly events. Choose one of them to decide what counts as activation, and send those events to your email tool. Do not let each team define activation separately.
Pricing: Amplitude pricing page and Mixpanel pricing page.
Stripe
Stripe is a payments provider and the source of trial and subscription status for many SaaS products. Its standard card pricing is per transaction and has no monthly platform fee, and it does not offer a permanent free plan. Stripe sends subscription events such as trial-ending notices and subscription changes, which your email tool or automation layer can use to suppress reminders after a payment. Read the webhook documentation before building trial logic, because the timing and retry behavior matter for suppression.
Pricing: Stripe pricing page.
What Trial Lists Cost at Realistic Sizes
| Tool | 1,000 contacts | 2,000 contacts | 10,000 contacts | 20,000 contacts | 50,000 contacts |
|---|---|---|---|---|---|
| Encharge (Growth) | $79/mo billed yearly ($99 monthly) | $79/mo billed yearly ($99 monthly) | Pricing on request | Pricing on request | Pricing on request |
| Customer.io (Essentials) | Pricing on request | Pricing on request | $145/mo billed monthly (10k profiles) | $235/mo billed monthly (20k profiles) | $505+/mo billed monthly (50k+ profiles) |
| Drip | $39/mo (1–2,500 people) | $39/mo (1–2,500 people) | $154/mo (9,001–10,000 people) | $289/mo (17,501–20,000 people) | $699/mo (45,001–50,000 people) |
| ActiveCampaign | Starter $15/mo, Plus $49/mo, Pro $79/mo | Pricing on request | Pricing on request | Pricing on request | Pricing on request |
| Userlist | Pricing on request | Pricing on request | Basic $149/mo; Professional $349/mo (up to 10,000 users) | Pricing on request | Pricing on request |
| Loops | Free (up to 4,000 sends per rolling 30 days to the newest 1,000 contacts) | Pricing on request | Pricing on request | Pricing on request | Pricing on request |
| Kit | Free (up to 10,000 subscribers, no sequences) | Free (up to 10,000 subscribers, no sequences) | Free (up to 10,000 subscribers, no sequences) | Pricing on request | Pricing on request |
Sizes are contacts, profiles, subscribers or users as each vendor counts them. "Pricing on request" means the vendor's published pricing does not give a price at that size. Intercom and HubSpot Marketing Hub are priced per seat or per plan, so they are not listed by contact count.
If You Need X, Pick Y
| If you need | Pick | Because |
|---|---|---|
| Trial paths that branch on product events | Customer.io | Event-driven triggers and a visual workflow builder, with A/B testing inside workflows |
| The lowest cost for a list under 2,000 subscribers | Encharge | Growth at $79/mo billed yearly, with unlimited flows and team members on that plan |
| A simple 14-day welcome-to-upgrade series with a free start | Loops | Free plan for up to 4,000 sends in a rolling 30 days, with transactional sends on paid plans |
| Team trials tracked at the company level | Userlist | Company-level segments and a Basic plan at $149/mo for up to 10,000 users |
| Trial deals handled by a sales team in a CRM | HubSpot Marketing Hub or ActiveCampaign | CRM records and workflows in one place; ActiveCampaign Pro starts at $79/mo for 1,000 contacts |
| In-app messages, product tours and chat during a trial | Intercom | Email, in-app and chat use the same user record, priced per seat |
| Billing events passed to an email sender on a small budget | Make or Zapier | Make's free plan has 1,000 credits a month; Zapier's free plan has 100 tasks a month |
| Suppression that stops reminders the moment a user pays | Any tool with a billing webhook or native billing connector | Suppression depends on how trial status reaches the sender, so check that route before choosing |
How to Choose for Your Trial
Start from the trial you run today, not the one you want in a year.
Begin with the length and shape of the trial. A 7-day trial with one core action needs fewer branches than a 30-day trial with a team invitation step. A short trial rewards speed, so the sequence needs to reach the user within the first day and the expiry reminders need to be fast. A longer trial can afford a mid-trial value email and a slower path, but it needs more branches to avoid sending the same message to every user.
Next, decide where trial status will come from. If your billing system is the source of truth, pick a tool with a native billing connector or one that accepts webhooks cleanly, and test the suppression case with a real trial conversion before you launch. If the status lives in your application database, pick a tool that accepts API events, and make sure someone owns the sync. If the status is a tag set by a person, expect it to fall out of date, and keep that in mind when you choose Kit or a similar tool.
Then decide who builds and edits the sequence. A single marketer can manage a linear series in Loops or Kit, but branching on product events usually needs an engineer for the first version and then a marketer for the copy. Encharge and Customer.io are designed for teams that split that work. ActiveCampaign and HubSpot suit teams that already have a CRM owner.
Finally, count the cost at the list size you expect in twelve months, not only the size you have today. A list that grows from 2,000 to 20,000 subscribers can move you from one pricing tier to another in a single quarter. Ask for a quote where the public pricing does not give one, and compare the total monthly cost of the sender plus the event tools you will need.
Trial Email Setup Checklist
| Step | What to set up | Where the data comes from |
|---|---|---|
| 1. Define trial state | Trial start, trial end, current plan, any extension, and a flag for converted users | Your billing system, for example Stripe subscription status and trial-ending events |
| 2. Name the activation events | Three to five actions that show a user has found value, written in one shared list | Product analytics such as Amplitude or Mixpanel, or your application database |
| 3. Send events to the sender | One event per action, with user ID, trial day and plan name attached | An API call, a native integration, or an automation tool such as Make or Zapier |
| 4. Build suppression | An exit rule that removes a user from every trial sequence when a payment event arrives | The billing webhook or connector. Test this with a real paid conversion before launch |
| 5. Build the branches | Separate paths for activated, stuck and dormant users | Activation events and trial day in the sender's workflow builder |
| 6. Protect transactional mail | Receipts, failed-payment notices and trial-ending confirmations on a route separate from marketing sends | The sender's transactional feature, or a separate transactional provider |
| 7. Clean addresses at signup | Basic format and typo checks on the sign-up form, and an address-validation step if you use a verification service | Your sign-up form, and a verification service if you add one. Encharge includes free email verification on its plans |
| 8. Set the win-back segment | Expired trials that did not convert, excluded from any active-trial sequence | Trial end date and conversion flag from step 1 |
Designing the Sequence Each Tool Runs
The tool matters less than the sequence you build in it. This is the structure that works across all of the tools above.
Day 1: one clear next step
The welcome email should name one action, usually the one that the activation list places first. A feature tour can wait. If the user has already completed that action by the time the email is due, the sender should skip it, which is only possible with activation events that reach the tool quickly.
Days 2 to 4: remove the blocker
Users who have not reached the first activation event need help with the step they are stuck on. Send a short note that links to the exact help page for that step, not the general documentation. Users who have reached it should get a different message that builds on what they did.
Middle of the trial: show the value that has been used
A short summary of what the user has done during the trial is more persuasive than a list of features. Keep the numbers in the email tied to the product's own data, and make sure each number is correct for that user. A wrong count sent to a user is worse than no count at all.
Final days: a clear deadline and a clear price
Send reminders before the trial ends and state the date the trial closes. Include the plan the user would move to and its price, with the billing cycle, so the user does not have to hunt for it. If you offer an extension, state the new end date. Stop all reminders the moment a payment event arrives.
After expiry: a short, separate win-back
Wait a few days after the trial ends before starting a win-back sequence, so that the message does not feel like a continuation of the trial. Lead with what has changed in the product, not with a request to come back. Keep the sequence short, and stop it after the last message rather than sending monthly reminders indefinitely.
Writing Upgrade Messages That Fit the Trial
An upgrade message works when it describes the user's own use of the product and the price that applies to them. Name the plan, the monthly or yearly price and the limit the plan lifts, such as the number of contacts or the number of workflows. A user on a 1,000-contact trial should see the price for the plan that covers 1,000 contacts, not a starting price for a much larger tier.
Avoid promotional adjectives and urgency that is not real. If the trial closes on a particular day, say so. If there is no discount, do not imply one. If an extension is available for certain users, make the eligibility clear in the message itself, so that a user who is not eligible does not feel misled when they click through.
Keep upgrade messages separate from educational messages in the sequence. Mixing a feature tour and a price in one email makes the price feel like the point of the tour. Give each email one job: help with the next step, show what has been used, or confirm the decision.
For products sold to teams, write the upgrade message for the person who pays, not the person who uses the trial most. Userlist's company-level view and HubSpot's deal stages both support this. Where the admin and the users are different people, send the admin a summary and the users a note that the team is on a trial, not a bill.
Where to Go Next
Compare the full set of tools
The main comparison page covers the same tools across more use cases, with the prices for each plan.
View the full comparisonBrowse every tool in the directory
The tools index lists each vendor covered on the site, with links to its pricing page.
Browse all toolsFrequently Asked Questions
Answers to the questions that come up most often when a SaaS team sets up trial emails.
Which tool should a small SaaS pick for trial emails?
It depends on the list size and the trial shape. For a list under 2,000 subscribers with a few behavioral branches, Encharge's Growth plan is $79 a month billed yearly. For a linear welcome series on a free start, Loops or Kit can do the job. For many branching paths driven by product events, Customer.io is the better fit, starting at $100 a month on its Essentials plan.
How do I stop trial emails once a user pays?
Use a payment event from your billing system to remove the user from every trial sequence. Stripe sends subscription events, including trial-ending notices, that can drive this. Test the case with a real paid conversion before the sequence goes live, because a missed event is the most common reason a paying customer gets a trial-ending email.
Do I need product analytics to run trial emails?
You need some source of activation events. That can be your application database, a product analytics tool such as Amplitude or Mixpanel, or a native integration. Amplitude's free plan includes 2M events a month, and Mixpanel's includes up to 1M, which is enough to start defining activation.
Is it worth paying for Make or Zapier?
Both are useful when a few billing or product events need to reach your email sender and no native integration exists. Make's free plan includes 1,000 credits a month, and Zapier's includes 100 tasks a month. Paid plans start at $9 a month billed yearly for Make's Core plan and $19.99 a month for Zapier's Professional plan. Once event volume grows, a native integration is usually cheaper and more reliable.
When should a win-back sequence start?
Wait a few days after the trial ends, so the message does not look like the last trial reminder. Lead with what has changed in the product, and keep the sequence short. Stop after the final message instead of sending indefinitely.
Should I offer a discount to trial users?
Use discounts for specific cases, such as an engaged user who has not converted by the trial end. A discount offered to everyone trains users to wait for one. If you offer an extension, state the new end date. Any offer should be easy to understand and easy to decline, and the message should show the price that applies after the offer ends.