To chase overdue invoices automatically, use the reminder feature your invoicing tool already has: turn on automatic reminders, choose when they go out (for example a few days before the due date, on the due date, and one and two weeks late), and rewrite the default message once so it sounds like you. QuickBooks Online, Xero, Stripe and Wave all have built-in scheduled reminders. AI is most useful for the wording, and for the personal follow-up once the automatic emails have run out.
The 2-minute answer
If you only have two minutes, do this:
- Make sure every invoice has a due date and goes to the right email address. Automatic reminders depend on both.
- Open your invoicing tool’s reminder settings (the exact steps for each tool are below) and switch them on.
- Pick two to four reminders, using the schedule below as a starting point.
- Replace the default text with a short, friendly message that includes the invoice number, amount, due date and a payment link.
- Keep your payments up to date in the tool, so paid customers stop getting reminders.
The rest of this guide shows where the switch is in each tool and what to do when reminders do not work.
A reminder schedule that works
There is no official rule for how many reminders to send. This is a sensible starting point that fits inside the limits of all four tools in this guide. Adjust it to your payment terms and your clients.
| When | Tone | What it says |
|---|---|---|
| 3 days before the due date | Friendly heads-up | Invoice number, amount, due date, payment link |
| On the due date | Friendly | ”Due today”, payment link, who to contact with questions |
| 7 days overdue | Polite, direct | Now overdue, amount, payment link, ask them to reply if there is a problem |
| 14 days overdue | Firm, still polite | Second overdue notice, asks for a payment date |
| After that | Personal | You email or call yourself (see the last section) |
QuickBooks Online allows three automatic reminders, so pick the three that matter most to you (many people drop the before-due one). Wave offers fixed options that match this table almost exactly. Xero and Stripe let you set your own days.
QuickBooks Online: where to turn it on, limits
According to Intuit’s help article for QuickBooks Online:
- Go to Settings, then Account and settings.
- Open the Sales tab and select Edit in the Reminders section.
- Turn on Automatic invoice reminders.
- Turn on Reminder 1 and choose how many days before or after the due date it goes out. You can add a second and third reminder.
- Edit the subject line, greeting and message for each reminder, then select Save and Done.
Limits worth knowing:
- Up to three automatic reminders.
- Each reminder can go out up to 90 days before or after the due date.
- QuickBooks only sends reminders for unpaid invoices you have already emailed from QuickBooks. If you send invoices another way, the automatic reminders will not cover them.
Intuit also notes that QuickBooks Online Advanced users can build reminders with workflows instead.
Xero: invoice reminders setup
Xero Central describes the setup like this:
- Open the Sales menu, select Invoices, then click the Invoice Reminders: Off button.
- Tick Email customers when an invoice is… and set when and how often reminders go out.
- Use Xero’s suggested message or write your own.
Limits worth knowing:
- Xero creates three default reminders when you first turn the feature on. You can edit or delete them and add more, up to five reminders in total.
- You can add a reminder that goes out before the due date.
- Reminders go to the contact’s primary person and anyone else marked Include in emails on the contact.
- Replies go to the email address of the user who turned reminders on, and you can change that address.
- You can stop reminders for a specific customer or invoice, for example one that is partly paid or that you have already discussed with the client.
- Xero says to connect your bank account so it stops sending reminders once payment arrives.
Stripe: automatic collection and reminder emails
Stripe has two different features.
Reminders for one-off invoices. In Stripe’s billing settings, open the Invoices tab, go to Manage advanced invoicing features and turn on Send reminders if a one-off invoice hasn’t been paid. Then click Add reminder for each email you want and pick a schedule. Reminders can go before, on or after the due date. Stripe skips a reminder if a payment on that invoice is already processing, so customers who have just paid are not nagged.
Automatic collection for card payments. If the customer pays by a saved card and the payment fails, Stripe can retry the card at chosen times (its Smart Retries feature) and email the customer when a card payment fails. That is for failed automatic payments, not for invoices a client simply has not paid.
Wave and others
Wave’s help center says you can schedule payment reminders if your business accepts online payments through Wave or is on its Pro Plan. You set default reminders under your business name, Business settings, Invoices and estimates, Reminder settings, and you can also set them per invoice. The options are fixed: 14, 7 and 3 days before the due date, on the due date, and 3, 7 and 14 days after. Reminders go only to the customer’s primary email, stop once the invoice is marked fully paid, and the default setting does not apply to recurring invoices.
Most other invoicing tools have a similar setting. Look for “reminders”, “payment reminders” or “dunning” in the settings or help center before you pay for a separate add-on.
Where AI helps (writing, tone, escalation)
The tools send the email. They do not make it sound like you. That is where an AI chat tool such as ChatGPT, Claude or Gemini earns its place: you describe the situation and it drafts a set of reminders with the right tone for each stage. Our guide to chasing an overdue invoice without the awkward email covers the wording in depth.
Try this prompt and fill in the brackets:
I run a [type of business]. Write [three] short payment reminder emails for my invoicing tool’s automatic reminders: one for [3 days before the due date], one for [the due date], and one for [7 days overdue]. Use these placeholders exactly as written so my tool can fill them in: [Invoice number], [Amount], [Due date], [Payment link]. Tone: friendly and professional, getting slightly more direct each time, never threatening. Each email under 90 words, with a clear subject line that includes the word “reminder”. Do not mention late fees or legal action.
Check the placeholder names against your tool’s own variables before you paste the text in. To make the drafts sound more like you, see how to teach AI to sound like you.
AI is also useful after the automatic reminders stop. Paste in the client’s history (what they bought, what they said, how late they are) and ask for a short personal note.
When to stop emailing and call
Automatic reminders are good at catching people who forgot. They are bad at the client who has a problem with the invoice, a cash flow issue or a missing purchase order number. If two or three reminders have gone out with no reply, stop the automatic emails for that invoice and contact the client yourself. A short call or a personal email that asks “Is anything holding this up?” often gets an answer that no template will. Our guide to follow-ups that don’t feel awkward has a script for that conversation.
If you are thinking about late fees or a collections agency, get advice from an accountant or a lawyer where you work. The rules depend on your contract and your country, and this guide does not cover them. For more admin time savers, browse our admin guides.
FAQ
Can QuickBooks chase overdue invoices automatically?
Yes. QuickBooks Online can send up to three automatic reminders, each up to 90 days before or after the due date. Turn them on in Account and settings, Sales, Reminders. They only go out for unpaid invoices you emailed from QuickBooks.
How do I set up automatic invoice reminders in Xero?
Go to Sales, Invoices, and click Invoice Reminders: Off. Tick “Email customers when an invoice is…” and set your schedule. Xero starts you with three default reminders, and you can have up to five.
Does Stripe send reminders for unpaid invoices?
Yes, for one-off invoices. Turn on “Send reminders if a one-off invoice hasn’t been paid” in the Invoices tab of your billing settings and add reminders before, on or after the due date.
How many reminders should I send for an overdue invoice?
There is no fixed rule. Two to four automatic reminders, from just before the due date to about two weeks late, is a reasonable start. After that, contact the client personally.
Can AI write my payment reminder emails?
Yes. An AI chat tool can draft a set of reminders that get firmer with each stage. Give it your business type, the schedule and your tool’s placeholders, then edit the result so it sounds like you.