threndle.ai · Guide · Updated October 15, 2026
How to automate overdue invoice reminders in QuickBooks, Xero and Square
QuickBooks Online, Xero and Square can all send overdue invoice reminders for you, and in each one it is a setting, not a project. QuickBooks sends email reminders up to 90 days before or after the due date (Intuit). Xero lets you create up to five reminders (Xero Central). Square lets you choose the reminder dates on each invoice (Square Support Centre, Canada).
Setup difficulty
1 of 5 for a first-timer
One settings screen in software you already use, then a message to edit. How we grade it.
This guide shows where the reminder setting is in each tool, how many reminders you get, the checks to do before you switch them on and what it costs to go further. It is written for small businesses in Chilliwack, Abbotsford, Langley, Agassiz, Hope and the rest of Canada. threndle.ai is an independent agency and is not affiliated with Intuit, Xero, Square or Anthropic.
Key takeaways
- QuickBooks Online: Settings, Account and settings, Sales tab, Reminders. Reminders go out only for invoices you have already emailed.
- Xero: three default reminders are set up for you, and you can create up to five. They go out for invoices marked as sent.
- Square: turn on payment reminders on the invoice and choose the dates.
- Match payments to invoices first, so nobody who already paid gets a reminder.
How do automatic invoice reminders work?
You set the rule once: how many days before or after the due date each reminder goes out, and what it says. The software checks your open invoices and emails the customer when one matches. Intuit says QuickBooks sends a reminder only when the invoice "hasn't been paid."
How do you turn on invoice reminders in QuickBooks Online?
These are Intuit's steps for QuickBooks Online in Canada (Intuit, "Send invoice reminders automatically or manually").
- Go to Settings and select Account and settings.
- Select the Sales tab.
- In the Reminders section, select the edit icon.
- 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 create second and third reminders as needed.
- Edit the subject and message. Intuit suggests keeping "reminder" in the subject, and you can add variables such as the invoice number and your company name.
- Select Save.
Intuit says QuickBooks sends a reminder only for invoices you have already emailed. To attach a PDF copy, turn on PDF Attached in the Online delivery section of the same Sales tab. On QuickBooks Online Advanced you can also build reminders with workflows, and you can set them up by asking Intuit Intelligence, QuickBooks' built-in assistant.
How do you turn on invoice reminders in Xero?
Xero has three default reminders set up for you. You only have to turn them on (Xero Central, "Set up and add invoice reminders").
- Check each customer has a current email address in your Xero contacts.
- Mark the invoices you want reminders for as sent.
- Click Invoice Reminders: Off to turn them on.
- Optional: include the online invoice link or a PDF link, or skip reminders for amounts under a figure you choose.
- Click Save. To add more, click Add reminder and enter the number of days before or after the due date. Set it to 0 to send on the due date. You can create up to five.
Xero says customer replies go to the login email of the person who first turned reminders on, and you can change that address.
How do you turn on invoice reminders in Square?
In Square, reminders are part of each invoice (Square Support Centre, "Create and send invoices").
- Create the invoice and choose how to send it: email, text message or share link.
- Tap Payment reminders and toggle Send payment reminders on.
- Choose the reminder dates.
Square's invoices page lists "Schedule automatic payment reminders" among its features (Square Invoices, Canada).
Which tool does what?
| Tool | Where you turn it on | How many | Goes out for |
|---|---|---|---|
| QuickBooks Online | Account and settings, Sales tab, Reminders | Reminder 1, plus second and third reminders as needed | Invoices you have already emailed, up to 90 days before or after the due date |
| Xero | Invoice Reminders | 3 default, up to 5 | Invoices marked as sent, to customers with an email address |
| Square | Payment reminders on the invoice | Dates you choose | That invoice |
What is the best way to automate overdue invoice reminders for QuickBooks?
Start with QuickBooks' own automatic reminders. They are a setting in QuickBooks Online itself, and they only go to invoices you have emailed that have not been paid. We suggest a second reminder a few days after the due date and a third, firmer one later.
Go further when one message for every customer is not enough: firmer wording for repeat late payers, a call list for anything long overdue, or reminders tied to your CRM. That is where a build comes in.
What should you check before you turn them on?
- Payments are matched. A reminder sent to a customer who paid by e-transfer that morning does damage, so match payments to invoices before reminders go out. More on this in our small business automation guide.
- Due dates are right. QuickBooks and Xero count each reminder from the invoice's due date.
- Customer emails are current. Xero needs one for each customer, and QuickBooks only reminds on invoices you emailed.
- Long overdue goes to you. We suggest routing anything more than 30 days overdue to yourself for a personal call.
Where does Claude fit?
Claude can find who is overdue and draft the follow-up for you to send. Through Composio, a connection service, Claude can run QuickBooks tools such as Aged Receivables Report and List Invoices (Composio QuickBooks toolkit). Composio's toolkit page lists no tool for sending an invoice reminder, so the send stays in QuickBooks or your email. To connect it, see our QuickBooks and Claude how-to.
What does it cost to automate payment reminders in BC?
The reminders above are settings inside software you already pay for. If you want us to build more, such as reminders tied to your CRM or different messages for different customers, our published pricing is on the homepage: a Foundation build for one bottleneck is typically $3,000 to $3,500, and every build carries a monthly care plan of $300 to $600, in Canadian dollars.
Who sets up invoice follow-up automation in the Fraser Valley?
threndle.ai is an AI automation agency in the Fraser Valley, British Columbia, working on site in Chilliwack, Abbotsford, Langley, Agassiz and Hope. We connect accounting tools such as QuickBooks, Xero, Wave, Sage and Zoho Books, payments such as Square, and CRMs such as HubSpot.
Frequently asked questions
How far ahead can QuickBooks send a reminder?
Up to 90 days before or after the invoice due date.
How many reminders can Xero send?
Xero sets up three default reminders, and you can create up to five.
Will a customer who already paid get a reminder?
Only if the payment is not recorded against the invoice. Match payments first.
Can Claude send the reminders?
Claude can find overdue invoices and draft the message through Composio. Composio's QuickBooks toolkit lists no send-reminder tool, so you send it from QuickBooks or email.
Can I turn QuickBooks reminders off again?
Yes. Turn off Automatic invoice reminders in the same Sales tab. Intuit says your customizations stay if you turn them back on.
What should you do first?
Match last week's payments, then switch on reminders in the tool you invoice from. To see where your own time goes first, try the 3-minute diagnostic, or book a meeting.
Sources
- Intuit, "Send invoice reminders automatically or manually in QuickBooks Online" (Canada), read October 15, 2026
- Xero Central, "Set up and add invoice reminders", read October 15, 2026
- Square Support Centre, Canada, "Create and send invoices", read October 15, 2026
- Square Invoices, Canada, read October 15, 2026
- Composio, QuickBooks toolkit, read October 15, 2026
- threndle.ai, What small business automations actually save time in BC?