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Looking for portal-initiated online payments? View Portals Overview (PayPal supported).
The TruckMaster + Square integration helps you send invoices through Square and accept online payments with less manual follow-up.
Customers receive the invoice via Square, pay through Square’s checkout, and the payment is credited back to the corresponding invoice in TruckMaster billing.
✅ Who it’s for: Carriers, brokers, and fleets that want to invoice customers via Square and keep payment status accurate inside TruckMaster TMS.
Invoice delivery & payment: Square ✔ | Portal-initiated payments: PayPal ✔ (Square —)
Result: Faster payments, fewer payment-status emails, and accurate invoice balances inside TruckMaster.
If you want customers to initiate payments directly from the TruckMaster customer portal, PayPal supports portal-based payments.
Request Square Integration SetupYes. TruckMaster sends invoices through Square as part of your billing workflow, and your customer receives the invoice from Square to pay online.
Yes. When the invoice is paid through Square, the payment is credited back to the corresponding invoice in TruckMaster so your invoice balance and payment status stay accurate.
No. Square payments are completed through Square (via the Square invoice). If you want portal-initiated online payments, PayPal supports payments initiated from the TruckMaster customer portal.
Typically no. Customers can pay using Square’s checkout experience (for example, by entering their payment method) based on your Square settings and the payment methods you enable.
Use the request form on this page, or contact TruckMaster support or your account manager to get started.