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Setting up Square terminals for in-person payments

How to connect a Square terminal for tap-to-pay at the front desk, and when to use it instead of Stripe.

Updated June 4, 2026

Stripe handles every online payment in Rosterra. Square is for in-person, card-present transactions at the front desk, where having a physical terminal is the right move.

When to use Square instead of Stripe

  • A parent walks in to pay tuition and hands you their card. A Square terminal accepts tap, chip, and swipe in seconds.
  • You sell gear at the front desk and want to ring it up like a retail store.
  • You want a printed receipt.

For everything else (online enrollments, parent portal payments, automated tuition charges), Stripe runs in the background and Square is not involved.

Connecting your Square account

  1. Go to /settings/payments-square and click Connect Square.
  2. Sign in to your Square account, or create one if you do not have it.
  3. Approve Rosterra to read and write to your Square account.
  4. You are redirected back. The connection is live.

Pairing a terminal

After the account is connected, register your physical terminals at /settings/square-terminals.

  1. Power on the terminal and connect it to your Wi-Fi.
  2. In Rosterra, click Pair terminal and pick the one that shows up.
  3. Give it a name (Front Desk, Main Mat, Pro Shop).

The terminal is now bound to your school. Multiple terminals are fine if you have more than one checkout.

Taking a payment

From any payment page in Rosterra (a tuition charge, a pro shop sale, a party balance):

  1. Pick Square terminal as the payment method.
  2. Choose which terminal.
  3. The terminal lights up with the amount.
  4. The customer taps, chips, or swipes.
  5. Rosterra records the payment immediately.

Refunds

Refund a Square payment from the original payment record in Rosterra. The refund goes back to the same card. The customer does not need to bring the card back; the original transaction ID is enough.

Disputes

Disputes on Square are handled inside the Square dashboard, not Rosterra. Square emails you when one opens. You upload your evidence (receipt, attendance record, signed waiver) directly to Square. Most disputes are resolved within 30 days.

Costs

Square charges its own processing fee per transaction. The current rate is on Square's website. Rosterra does not add a fee on top.

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Setting up Square terminals for in-person payments · Help center · QuickKicks