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Can I prompt the customer to use the existing card I have on file for them?
You can create an experience where you get the customer's mobile number and then ask: “You have the card ending on *3434 on file. Would you like me to bill that card?”
The merchant is able to configure multiple payment options on an Order Management System (OMS). As an example, the screenshot below shows a merchant where Chat 2 Pay is just one of many configured payment options.

Chat 2 Pay appears as one of the payment options available to the customer service agent
If the merchant already has a card-on-file (COF) associated with the Customer, the merchant triggers a COF payment method (i.e., the “Credit Card” option on the example above) on the OMS rather than the Chat 2 Pay payment method.
If the merchant doesn't have a COF or uses a system that doesn't display COF, then the merchant uses the Chat 2 Pay payment method to deliver a payment link to the customer. The customer uses the payment link and associated checkout page and is given the option to save a new card on file using either
Cybersource’s Token Management Service
Visa’s Click to Pay Wallet
MasterCard’s Masterpass Wallet
A 3rd party Token Vault configured on the merchant’s Cybersource configuration

Payment screen where the customer can add a new card or select a saved card from their Visa Click to Pay wallet
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