How to Automate Payment Reminders in Stripe and Stop Chasing Invoices
If you run a service-based business, you know the pain of chasing late invoices. It drains time, energy, and focus that should be going into client work or growth. The good news? Stripe has built-in automation features that can recover failed payments and send reminders for you — so you stop being the bill collector and start getting paid on time.
In this guide, I’ll show you how to automate payment reminders in Stripe, recover failed payments, and set up dunning emails that sound human (not robotic). Plus, you’ll get copy-paste email snippets you can drop straight into your Stripe setup.
Why Automating Payment Reminders Matters
No more awkward chasing: Stripe does the nudging so you don’t have to.
Healthier cash flow: Reduce failed payments and late invoices.
Time saved: Put your focus back on client work instead of admin tasks.
If you’ve ever Googled “how to stop chasing invoices” or “automate failed payment recovery in Stripe”, this post is your pain-killer solution.
Step 1: Enable Smart Retries in Stripe
Stripe’s Smart Retries automatically attempts to charge a failed payment again. Instead of retrying at random, Stripe uses machine learning to pick times when the payment is most likely to succeed.
How to set it up:
Go to Settings → Billing → Subscriptions and emails in your Stripe dashboard.
Under Manage failed payments, toggle on Smart Retries.
Decide how many days you want Stripe to retry before marking the invoice as uncollectible.
Step 2: Turn On Automated Dunning Emails
Dunning emails are the polite reminders Stripe sends when a payment fails. These can go out instantly and at intervals you choose, reducing the chance of lost revenue.
How to set it up:
In Settings → Billing → Subscriptions and emails, scroll to Email customers about…
Turn on Upcoming renewal and Payment failed notifications.
Customise the copy so it matches your brand tone — warm, firm, or casual.
Step 3: Use Stripe Subscriptions for Predictable Revenue
If you offer ongoing services, Stripe Subscriptions automate the billing cycle entirely — invoices, payments, and reminders happen without you lifting a finger. Subscriptions also work seamlessly with Smart Retries and dunning emails.
Copy-Paste Email Snippets for Stripe Dunning Emails
Want higher recovery rates and longer dwell time? Start with these templates, then adjust the tone to match your brand.
Failed Payment Reminder #1 (Friendly)
Subject: Oops — Looks like your payment didn’t go through
Hi [First Name],
Just a quick heads up that your recent payment attempt didn’t go through. No worries, this happens sometimes! You can update your card details here: [payment link].
We’ll automatically retry your payment in the next couple of days, so updating your info now ensures no interruption to your service.
Thanks so much,
[Your Name]
Failed Payment Reminder #2 (Firm but Polite)
Subject: Action needed: Please update your payment details
Hi [First Name],
Your payment for [service/product] has failed a second time. Please update your payment details here: [payment link] to avoid suspension of service.
If you have any questions, just hit reply and we’ll help right away.
Thank you,
[Your Name]
Upcoming Payment Reminder
Subject: Your upcoming payment is due soon
Hi [First Name],
This is a quick reminder that your payment for [service/product] will be processed on [date]. If you’d like to update your payment method, you can do so here: [payment link].
Thank you for being a valued client!
Best,
[Your Name]
Final Word
Chasing invoices doesn’t have to be part of your job description. With Stripe’s automation — Smart Retries, dunning emails, and subscriptions — you can stop worrying about cash flow interruptions and focus on delivering your service.
Set this up once and you’ll thank yourself every month.
