Chat-based transaction automation system

A computing system implementing an automated peer-to-peer (P2P) transaction service, comprising:

• network communication interface to communicate, over one or more networks, to computing devices of a plurality of users of a transaction service;
• one or more processors;
• and
• a memory storing instructions that, when executed by the one or more processors, causes the computing system to:
• maintain a digital wallet for each respective user of the plurality of users by connecting an external account of the respective user to the digital wallet;
• transmit, over the one or more networks, display data to a computing device of the respective user, the display data causing a customized user interface (UI) for the respective user to be displayed on a display screen of the computing device of the respective user to enable access and utilization of the digital wallet, the customized UI comprising at least (i) a selectable authorization feature to automatically authorize transactions from the digital wallet, and (ii) a transaction request feature to configure transaction requests for other digital wallets of the transaction service;
• receive, over the one or more networks, authorization data indicating a selection by the respective user of the selectable authorization feature in connection with a received transaction request from a computing device of a second user, the second user having a second digital wallet associated with the transaction service;
• and
• based on the authorization data, automatically execute a transaction from the digital wallet of the respective user to the second digital wallet of the second user in an amount indicated in the received transaction request.