To handle subscription billing with Square, start with native Square Subscriptions for simple recurring tasks. For more complex needs—such as custom membership programs, tiered plans, or customer-managed profiles—third-party apps like PayWhirl, Submatic, and Subport are highly effective options that integrate directly into the Square ecosystem.
3PayWhirlIdeal for businesses requiring robust features like customer self-service portals, tiered billing tiers, and usage-based pricing that exceed Square's baseline subscription capabilities.44%
Several software and app solutions integrate directly or via API/marketplaces with Square POS to handle recurring subscription billing, memberships, and repeat invoicing.
Subport — A dedicated subscription and membership management tool available directly in the Square App Marketplace . It lets sellers create tiered subscription programs, credits, and recurring service offerings integrated straight into Square.
SubscriptionFlow — A comprehensive recurring billing and subscription management platform that integrates with Square POS. It allows you to sign up and process initial subscription payments right at your physical checkout counter using Square POS, while automating subsequent recurring billing cycles through .
ChatGPT Search· Sep 29, 2026
I’ll check current Square integrations and distinguish native subscription billing from third-party software that connects to Square POS.
Use Square’s own subscription billing — Square POS already supports recurring subscriptions, recurring invoices, trials, pauses/resumes, and scheduled billing. Square’s current Subscriptions API can also be integrated into custom software.
Submatic — Listed on the Square App Marketplace , this app is designed to handle memberships, recurring subscription packages, and automated repeat payments for service-based or retail businesses.
Invoicing platforms (like FreshBooks or Wave) — General accounting and invoicing tools offer recurring invoice scheduling and connect with Square's payment ecosystem to charge clients on a repeating cycle.
If you can share what type of business you run (e.g., retail, a service-based business, or a digital SaaS) and where you need the subscriptions managed (in-store POS vs. online), I can recommend the best-suited platform for your workflow.
Yes. If you mean software that can handle recurring/subscription billing while working with Square POS, there are two main approaches:
Square Subscriptions — Square itself supports recurring billing, including weekly, monthly, quarterly, and annual schedules, and subscriptions can be managed through Square Dashboard/POS. It also supports checkout links, QR codes, and online signup.
Square Recurring Invoices — useful when subscriptions are essentially recurring charges for services. Customers can have their card on file charged automatically according to the recurring schedule.
Custom software using Square's Subscriptions API — if you need more sophisticated subscription management, a developer can build a system around Square's API. Square supports creating, pausing, resuming, canceling, swapping, and managing subscription plans programmatically.
What about Chargebee, Recurly, etc.?
Platforms such as Chargebee and Recurly are strong subscription-management systems, but their documented payment-gateway integrations center on processors such as Stripe rather than simply plugging into Square POS as a subscription layer. For example, Chargebee documents Stripe as its payment gateway, while Recurly similarly documents Stripe integration.
So if your requirement is specifically:
"Customer buys a subscription at my physical business through Square POS, and the subscription automatically bills them later."
I'd first look at Square's native Subscriptions functionality rather than adding another billing platform.
If you tell me what kind of business you have (gym, salon, restaurant, membership club, recurring service, etc.) and whether you need membership management, automatic card billing, prorating, upgrades/downgrades, failed-payment recovery, or customer self-service, I can identify the Square-compatible software options that fit.
If you are looking to set up recurring or subscription billing that integrates with Square POS, there are several dedicated third-party apps and extensions designed to sync smoothly with Square's ecosystem.
Top software options that integrate with Square for subscription billing include:
PayWhirl : One of the most popular recurring billing extensions for Square. It lets you sell subscriptions, memberships, and recurring service packages directly through your Square-integrated store or website. It handles customer-facing billing portals, automated charging, and card-on-file updates.
Subport : Built specifically for Square sellers (ideal for cafés, local services, and membership offerings). It allows you to create tiered subscription programs, track usage, and automate billing directly within your workflow without requiring external checkout links.
Billforward : A robust subscription management platform that links with Square to handle complex recurring billing scenarios. It supports flexible billing periods (daily, weekly, monthly), free trials, tiered usage, and can register customers and take payments both online and in-person.
If you share what kind of business you run (e.g., retail, a service-based business, a gym, or a digital offering) and whether you need in-person or online subscriptions , I can help you pick the best-fit tool and outline how to set it up.
If you are looking to set up subscription billing or recurring payments that integrate directly with your Square POS or Square account, several specialized software options and built-in features are available depending on your exact business model:
1. Dedicated Apps in the Square App Marketplace
If you want robust subscription management that natively syncs with your Square catalog, customer lists, and inventory, you can use these dedicated marketplace integrations:
PayWhirl : Great for e-commerce and online setups. It allows customers to manage and customize their own subscriptions, saves payment methods on file, handles automatic billing, and integrates seamlessly with Square checkouts.
Subport : Ideal for retail, cafés, local services, and medspas. It lets you offer tiered subscriptions, memberships, or product subscriptions while automating recurring payments and syncing directly with your Square item database.
Subscriptions Cloud : Enables basic recurring sales, combination/subscription boxes, and mixed carts (allowing customers to buy subscription items and one-time products in a single checkout).
Submatic : Focuses heavily on local businesses, memberships, service packages, and recurring customer retainers.
2. Built-in Square Tools
Square Recurring Invoices : If your subscription model involves a fixed amount billed weekly, monthly, or yearly to regular clients (like a fixed retainer or simple membership fee), you can use Square’s native Square Invoices feature combined with Card on File to automatically charge clients on a recurring schedule without needing a third-party app.
3. Enterprise & Advanced Billing Platforms
Chargebee : A heavier, enterprise-grade recurring billing and subscription management platform. Chargebee supports various payment gateways, including Square and Stripe, making it a solid option if you need advanced proration, multi-tiered SaaS billing, or complex revenue recognition workflows.
Maxio : Another advanced subscription management and financial operations tool that connects with Square to streamline complex recurring billing models.
If you can share what type of business you run (e.g., retail products, digital SaaS, local services/gym) and whether the billing happens online or in-person , I can recommend the most seamless integration for your workflow.
Use a third-party subscription/membership platform that connects to Square — useful if you need more sophisticated membership management, recurring billing logic, customer portals, or industry-specific features.
A few things to consider before choosing one:
Option
Square integration
Best suited for
Square Subscriptions
Native
Straightforward recurring memberships/services
Square Invoices / Recurring Invoices
Native
Recurring charges where invoices are appropriate
Custom software via Square API
API
Highly customized subscription workflows
Third-party membership software
Varies by vendor
Gyms, clubs, classes, memberships, etc.
Square's API supports creating, changing, pausing, resuming, canceling, and swapping subscription plans, so a third-party application can build fairly sophisticated workflows around Square.
If you tell me what kind of business you have (e.g., gym, salon, SaaS, service business, nonprofit) and whether you need membership management + billing or billing only, I can give you a shortlist of specific software that integrates with Square and compare their pricing/features.
Yes. If you mean software that can use Square POS/payments to charge customers on a recurring subscription, there are several options.
Square Subscriptions — Square’s built-in option. It supports recurring weekly, monthly, biweekly, quarterly, semiannual, and annual billing, plus trials, pauses/resumes, checkout links, and recurring invoices.
Submatic — A Square App Marketplace integration specifically for memberships, passes, clubs, and subscription programs. Customers can buy memberships through Square POS or an online membership page, with benefits attached to their Square customer accounts.
MemberPress — Useful if you have a WordPress website and want memberships/subscriptions. Its Square integration supports recurring payments, trials, refunds, pausing/resuming subscriptions, and payment-method updates.
Custom software using Square's APIs — If you need a more specialized subscription system, Square provides a Subscriptions API for creating plans, billing customers on a recurring cadence, and managing subscriptions.
Which type fits?
If you need...
Consider
Simple recurring charges
Square Subscriptions
Gym/club/membership benefits tied to POS
Submatic
Paid memberships on a WordPress site
MemberPress + Square
Highly customized subscription logic
One important distinction: Square itself may already do what you need, so you may not need another billing platform. Square lets subscription plans be sold through POS and managed from Square Dashboard, although some subscription features have limitations.
If you tell me what kind of business you have (e.g., gym, salon, restaurant, SaaS, service business) and whether customers need to sign up online, at the POS, or both, I can narrow this down to the most suitable 2–3 options.
Several software solutions integrate with Square POS to handle subscription billing, recurring payments, and membership management. Depending on whether you are looking for an in-house app from the Square ecosystem, an e-commerce subscription manager, or a full enterprise billing platform, here are the top options:
PayWhirl : Available directly via the Square App Marketplace , PayWhirl lets you set up flexible subscription plans, recurring billing schedules, and customer self-service portals where clients can manage their saved cards and subscription history.
Subport : Found on the Square App Marketplace , this app is tailored for local businesses, cafes, and service providers (like medspas or clinics) wanting to run tiered membership programs and recurring orders directly tied into Square.
SubscriptionFlow : A robust recurring billing platform that integrates with Square POS to let you sign up and process subscriptions right at your physical checkout counter rather than forcing customers online.
Zoho Billing (formerly Zoho Subscriptions) : Part of the Zoho ecosystem, it provides automated recurring invoicing and subscription management, and it connects with Square for payment handling.
Chargebee & Maxio : Excellent for larger or B2B/SaaS-focused subscription models needing complex recurring billing, proration, and revenue recognition that can tie into the wider Square ecosystem.
Square Subscriptions (Native) : Don't overlook Square's own built-in tool, Square Subscriptions , which allows you to set up basic recurring invoices and customer card-on-file billing straight from your Square Dashboard and POS.
To help narrow down the best fit, could you tell me:
Are you looking for in-store/POS subscription signups , or online/e-commerce recurring billing?
What type of business do you run (e.g., retail, service-based, SaaS, food/bev)?
Several software solutions integrate directly with Square POS or use Square as a payment gateway for subscription and recurring billing. Depending on whether you are running an online store, a physical storefront/cafe, or an automated service business, here are the top choices:
PayWhirl — A popular subscription and recurring billing app built specifically to integrate with Square and Square Online. It lets you set up customizable billing schedules, customer self-service portals, automated retries for failed payments, and subscription discounts without custom coding. You can find it on the Square App Marketplace - PayWhirl.
Subport — Designed specifically for Square sellers (such as cafes, restaurants, and local services) wanting to offer memberships, tiered subscription packages, and credit systems natively tied into their operations. It automates recurring billing while letting customers redeem subscriptions across multiple Square locations. Check out the Square App Marketplace - Subport.
SubscriptionFlow — A robust, enterprise-grade recurring revenue platform that connects with Square to handle end-to-end subscription lifecycles, advanced dunning management, and automated invoicing. It is a strong option if you want to capture in-person subscription signups at a physical checkout counter and manage subsequent recurring cycles through an automated dashboard. More information is available on SubscriptionFlow.
Square's Native Subscriptions — Don't overlook Square's own built-in tools. Square Invoices allows you to set up recurring invoices and keep cards on file to automatically charge customers on a regular frequency without needing a third-party add-on.
If you can share what kind of business you run (e.g., retail, SaaS, a local service, or a restaurant/cafe) and how you plan to sign up subscribers (in-person at the POS vs. online), I can help you pick the best fit for your workflow.
Yes. If you use Square POS, you have several options for subscription/recurring billing:
Square Subscriptions — the simplest option. Square has native subscription management with weekly, monthly, quarterly, and annual billing, trials, pauses, plan changes, and recurring invoices. It works directly with Square POS and Dashboard.
Submatic — a Square App Marketplace integration aimed specifically at memberships, passes, clubs, and recurring programs. Customers can purchase memberships through Square POS or an online membership page, with benefits attached to their Square customer accounts.
Custom software using Square's Subscriptions API — useful if you need a customized membership/subscription system. Square's API can create, pause, resume, cancel, and modify subscriptions while using Square for the actual recurring payments.
Square Recurring Invoices — good if you don't need a formal "membership" system and simply want to charge customers automatically on a recurring schedule.
Which I'd choose
Need
Best option
Simple recurring memberships
Square Subscriptions
Gym/salon/club/mug club-style memberships
Submatic
Recurring service invoices
Square Recurring Invoices
Highly customized subscription software
Square Subscriptions API
One important distinction: if by "integrate with Square POS" you mean a separate membership/billing platform that syncs customers, memberships, and payments into Square, rather than simply using Square's own subscription functionality, I can give you a shortlist of 5–10 third-party platforms that integrate with Square POS, including pricing and what each syncs.
