21 October 2026Automation4 min read

Chasing unpaid invoices automatically, without damaging the relationship

Nobody likes chasing a customer who does not pay. So we postpone, wait for month end, and a 45-day invoice becomes a 90-day one. Reminders are the ideal task to automate: repetitive, dated, stable rules. Provided you know where the machine stops.

The schedule

  1. Three days before the due date: a courteous reminder with the invoice and a payment link.
  2. The day after the due date: “unless we are mistaken”, with the invoice.
  3. Fifteen days after: a firmer reminder mentioning the late-payment terms in your conditions of sale.
  4. Thirty days after: no more automation. A person calls.
A reminder sent on time is polite. The same one, a month late, is a reproach.

Stop rules

One reminder sent to a customer who paid yesterday costs more than ten forgotten ones.

Tone

Short messages, signed by a person, with the invoice and a one-click way to pay. No legal jargon before the third reminder.

Free 30-minute audit

We look at your real processes and tell you what is worth automating, and what is not. Pick a slot →

What stays human

The thirty-day call, negotiating a payment plan, deciding to go to collection. The machine sends reminders on time; it does not decide what happens next in a business relationship.

Before automating

You need a reliable source for “paid”: your invoicing software, your bank or your payment tool. If the paid status is updated by hand once a month, the automation will chase customers who have paid. Make that status reliable first.

Frequently asked questions

How do you automate unpaid invoice reminders?

With a fixed schedule (reminder before the due date, reminder the day after, firmer reminder at fifteen days), a payment status check right before each send, and stop rules: invoice paid, customer reply or pause by the team.

When should automatic reminders stop?

As soon as the invoice is paid, even partly, as soon as the customer replies or disputes, and at the latest around thirty days late, when a person should call.

What do you need before automating reminders?

A reliable payment status source: invoicing software, bank or payment tool. If that status is updated by hand once a month, the automation will chase customers who have paid.

Read next

Free cost calculatorWhat reminders and your other repetitive tasks cost you. What automating really costsThe four items of the real cost.

Are your reminders going out late? The free audit takes thirty minutes: we look at where your invoices' payment status comes from and what it would take for reminders to go out on their own.

Book a free audit↗

The TAKIA letter

One letter a month, nothing else

What we actually automate for our clients: what works, what breaks, what it costs. Written by the people who build the systems, not by a marketing team.