How to Set Up Recurring Payments on Square | Steps | Best Practices

If you’re a small business owner, freelancer, or service provider, keeping track of recurring transactions can make a major difference to your cash flow. Whether you’re billing clients monthly or paying vendors on a fixed schedule, having a system that handles repetitive payments automatically saves time and reduces errors.

In this guide, we’ll show you how to set up recurring payments on Square to receive money from customers or send payments to others. We’ll also walk through how to make things easier if your customers are based overseas, because recurring payments don’t need to stop at the border. We'll also talk about how Wise Business could help your company save when doing business internationally.

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What Are Recurring Payments?
Recurring payments are automatic transactions that repeat on a predefined schedule. There are two main types:
1. Income recurring payments: You receive payment from clients or customers on a recurring basis, like monthly retainers, subscriptions, or installment plans.
2. Outgoing recurring payment: You send payments regularly to vendors, contractors, or service providers, like software subscriptions or freelance teams.

With the right setup, you can automate both incoming and outgoing automatic payments.

Why Use Square for Recurring Payments?

Square offers user-friendly tools to manage invoicing and payments, including a recurring option that doesn’t require coding or complex software. That simplicity makes it ideal for small businesses and freelancers.

Some benefits of Square recurring payments include:

• Simple interface to create and manage invoices
• Support for credit card, ACH, Apple Pay, and Google Pay
• Automatic billing and payment reminders
• Easy integration with your contact and product list
• A mobile-friendly app and web dashboard

Note: Square processes payments in USD. While international customers may be able to pay using supported cards, Square doesn’t offer multi-currency invoicing. This can be a challenge for global businesses.

How to Set Up Recurring Payments on Square

Square makes it easy to set up Square automatic payments using the invoice tools. Here’s how to set up recurring payments on Square step-by-step:

Steps to Set Up Recurring Payments on Square	Description
Step 1: Sign in to your Square dashboard	Head to squareup.com and log in to your account. If you’re new, you’ll need to create a business profile first.
Step 2: Navigate to invoices	From the main menu, click Orders & Payments, then Invoices, and select Create Invoice.
Step 3: Choose ‘Recurring Invoice’	In the invoice form, choose Recurring instead of a one-time invoice. This allows you to schedule the invoice to go out at regular intervals.
Step 4: Set your schedule	Choose how often you want the invoice to be sent: Weekly, Monthly, Quarterly, Annually. You can also specify a start and end date, or keep it going indefinitely.
Step 5: Add customer details	Select an existing customer or create a new one by adding their name and email. If you want to set up Square automatic payments, ask the customer to save their card on file.
Step 6: Add your items or services	Input what you’re charging for, such as consulting services, product subscriptions, or retainers. Add tax and any applicable discounts.
Step 7: Enable automatic payments (optional)	If the customer has authorized card-on-file payments, you can toggle on “Automatically charge payment method on file.”
Step 8: Finalize and send	Add a personalized message if you’d like, then click Schedule to activate your Square recurring invoice.¹

What Happens After You Send a Recurring Invoice?

After sending a recurring payment, the following may happen:

• Your customer gets an email with the invoice.
• If they haven’t saved a card on file, they can pay it manually.
• If they have saved a card on file, Square will auto-charge them on each scheduled date.
• You’ll get notified when the payment is completed or if it fails.

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Save Time and Money On Overseas Payments With Wise Business

Wise Business can help you save big time on international payments.

Wise is not a bank, but a Money Services Business (MSB) provider and a smart alternative to banks. The Wise Business account is designed with international business in mind, and makes it easy to send, hold, and manage business funds in currencies.

Signing up to Wise Business allows access to BatchTransfer which you can use to pay up to 1000 invoices in one go. This is perfect for small businesses that are managing a global team, saving a ton of time and hassle when making payments.

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Some key features of Wise Business include:

• Mid-market rate: Get the mid-market exchange rate with no hidden fees on international transfers

• Global Account: Send money to countries and hold balances in multiple currencies, all in one place. You can also get major currency account details for a one-off fee to receive overseas payments like a local

• Access to BatchTransfer: Pay up to 1000 invoices in one click. Save time, money, and stress when you make 1000 payments in one click with BatchTransfer payments. Access to BatchTransfer is free with a Wise Business account

• Auto-conversions: Don't like the current currency exchange rate? Set your desired rate, and Wise sends the transfer the moment the rate is met

• Free invoicing tool: Generate and send professional invoices

• No minimum balance requirements or monthly fees: US-based businesses can open an account for free. Learn more about fees here

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How to Manage Outgoing Recurring Payments

While Square is mostly used to receive money, many businesses also need to send recurring payments, for example, to suppliers or remote teams.

Square itself doesn’t support sending recurring payouts or direct vendor payments, but there is an alternative.

Use Square Virtual Terminal for ad-hoc vendor payments

If your vendor accepts card payments, you can use Square Virtual Terminal to manually enter card details and make payments from your browser. This isn’t automated, but it can work for occasional recurring bills.

To edit, end, or view recurring invoices, do the following:

Step 1: Sign in to the Square dashboard

Sign in to the Square Dashboard.

Step 2: Navigate to invoices

Go to Orders & payments, click Invoices, and then select Recurring series

Step 3: Modify recurring invoices

Click (⏺⏺⏺) next to the recurring series or click into the recurring series to modify. Then choose to edit, view, or end the recurring series.

When editing an active recurring series, the edits will apply to all future invoices. When ending a recurring series, no future invoices will be sent from this series. However, outstanding invoices will apply.¹

Can You Use Square for International Recurring Payments?

You can technically use Square for international recurring payments, but there are a few things to be aware of.

Square accepts international card payments only if:

1. You’re based in an eligible country (like the US, Canada, or the UK)
2. Your customer is using a card supported by Square
3. You’re charging in your local currency (e.g., USD)

So if your client is in Europe or Asia and wants to pay with a non-US card, they may still be able to, but currency conversion fees could apply, and there may be some hiccups if their bank flags the transaction.

Best Practices for Recurring Payments

Whether you’re receiving or sending funds, there are a few tips to keep in mind when learning how to set up recurring payments on Square.

Keep customers informed

Always let your customers know:

• What the recurring charge covers
• When they’ll be charged
• How to cancel or update their payment method

Your customers want to know what they’re being charged for, when the charge will occur, etc. Transparency builds trust and helps reduce chargebacks or confusion.

Offer easy cancellation or adjustments

If you bill clients monthly, give them a clear way to cancel or pause their subscription. This will help prevent disputes and keep your business reputation strong.

Monitor payment failures

Square will alert you if a payment fails, but you should follow up quickly to avoid gaps in cash flow.

Automate where possible

Use card-on-file billing and batch payouts to streamline your system. Automation helps reduce human error and saves time.

Review your setup quarterly

Check if your recurring invoices or outgoing payments still reflect your pricing, terms, or vendor arrangements. Adjust as needed.

Additional Considerations for Managing Recurring Payments

To get the most out of your recurring payment processes, consider the following.

Implement Tiered Pricing Models

Offering customers tiered pricing can help expand your business to a wide customer base. For example, using Square’s Subscriptions API, you can create up to four pricing tiers, each with varying features and price points. Giving customers this flexibility to choose a plan that fits their needs and budget increases customer retention and satisfaction.

Use Analytics for Customer Insights

Analytic tools give you the leverage you need to understand customer payment behaviors. Learning patterns such as peak payment times, common payment failures, or subscription cancellations can give you valuable insights that can help you improve customer service and reduce churn.

Offer Multiple Payment Methods

Providing various payment options, including credit/debit cards, ACH transfers, and digital wallets, can enhance customer convenience. The more flexible your payment options, the more accessible your services become to a diverse customer base.

Final Thoughts

Learning how to set up recurring payments on Square can give your business predictable cash flow and fewer admin headaches. Whether you’re charging monthly retainers, offering subscriptions, or paying your remote team, automation matters.

• Use Square recurring invoice features for easy customer billing
• Enable Square automatic payments by requesting card-on-file access
• Send money abroad more affordably using Wise Business

Recurring doesn’t have to mean complicated. With the right setup, you can spend less time chasing payments and more time growing your business.

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Sources:

1. Create and send recurring invoices | Square Up