Improve Square's Invoices, Package Checkout & Order Management for Service-Based Businesses

[Modifi]

We operate a medical aesthetics and wellness business that relies heavily on Square Appointments, POS, Invoices, Packages, and Orders.

While Square offers many useful features individually, we're experiencing several significant limitations when trying to use them together. These issues create unnecessary administrative work, complicate reporting, and make certain features difficult to use in everyday operations.

We would like Square to consider the following improvements:

1. Recognize Partial Invoice Payments in Sales Reports

We offer 3- and 6-month programs with installment payment schedules.

Currently, when a customer makes a partial payment toward an invoice, that payment does not appear in our Sales Summary until the entire invoice has been paid.

This creates a significant reporting problem. We may collect payments over several months, but the associated sale is not reflected in Sales Summary until the final installment.

Requested Improvement: Allow individual installment payments to be reflected in appropriate sales and payment reporting when received, while preserving the original invoice, payment history, and outstanding balance.

2. Add Automatic 28-Day Payment Schedules With Flexible Amounts

Our programs require payments every 28 days, not every calendar month.

We currently have to manually configure payment dates because Square doesn't provide a convenient automatic four-week interval within a single invoice payment schedule.

Additionally, installment amounts may change during a program, so we need the flexibility to adjust future payment amounts without disrupting previously completed payments.

Requested Improvement: Allow businesses to select recurring installment intervals such as every 7, 14, or 28 days within one invoice, with independently adjustable payment amounts and deposits.

3. Allow Multiple Package Redemptions and Add-Ons in ONE Appointment Checkout

This is one of our biggest frustrations with Square Appointments and Packages.

Customers frequently receive multiple services during a single visit. Some services are covered by prepaid packages, while others are additional paid services or add-ons.

Currently, our workflow requires separate appointments and checkout transactions to properly redeem package credits and charge additional services.

This is extremely inefficient and makes Square's package functionality practically unusable for businesses that offer multiple treatments during one appointment.

Requested Improvement: Allow multiple services, prepaid package redemptions, and paid add-ons to be processed in ONE appointment and ONE checkout transaction, with the correct package credits automatically deducted.

4. Support Credit Card Surcharges on Invoice Payment Schedules

Square's automatic surcharge functionality does not support invoices with installment payment schedules.

Businesses using these invoices cannot apply the same automatic, compliant surcharge functionality available through certain other Square payment workflows.

Requested Improvement: Extend automatic surcharge functionality to eligible invoice installments, subject to applicable card-network rules, regulations, and permitted limits.

5. Add Automated Package Expiration Reminders

We sell prepaid treatment packages that customers may redeem over several months.

We would like Square to automatically notify customers when their purchased packages are approaching expiration, particularly when unused sessions remain.

Requested Improvement: Allow businesses to configure automatic reminders, such as 30 days before package expiration, showing customers their remaining sessions and expiration date.

6. Improve Invoice-to-Order Fulfillment Integration

Square allows shipping orders to be generated from invoices, but there is no equivalent straightforward workflow for automatically creating pickup orders from paid invoices.

Businesses accepting remote payments for products requiring later fulfillment would benefit from greater flexibility.

Requested Improvement: Allow paid invoices to automatically generate either shipping or pickup orders, with accurate fulfillment statuses and no duplicate transactions.

Why These Improvements Matter

For service-based businesses, Square is more than a payment processor. It is the system we depend on to manage appointments, customer packages, ongoing programs, billing, and fulfillment.

These features need to work together seamlessly.

We appreciate the capabilities Square provides, but these limitations create unnecessary workarounds, additional transactions, and reporting complications.

Our request is for better integration and flexibility across Square's existing features—not necessarily entirely new products.

These improvements would significantly benefit medspas, wellness clinics, salons, fitness studios, and other businesses offering prepaid services, installment programs, and multiple treatments per visit.