Flywire deployed CashMatch AI, a feature of its Invoiced by Flywire platform, that automatically matches incoming payments to open invoices without human intervention. The system handles complex scenarios like partial payments, overpayments, and missing remittance details, assigning a confidence score to each match.

CashMatch AI reads incoming payment amounts, payer identity, and remittance data, then auto-applies payments to open invoices with a confidence score from 1–100%. High-confidence matches are applied automatically; low-confidence matches are flagged for human review. The feature is part of Invoiced by Flywire, an AI-native accounts receivable platform acquired by Flywire in August 2024 for approximately $51.7 million. Prior to machine learning, Flywire's own announcement noted that legacy rules-based systems required 'significant manual effort to review transaction records and reconcile payments.'