Abstract: Technologies for automatically managing chargebacks include a chargeback processing server for receiving a chargeback corresponding to a disputed payment vehicle transaction and analyzing chargeback data as a function of historical chargeback win data and transaction-specific economic feasibility data. The chargeback processing server automatically determines, based on the analysis of the chargeback data, whether further review of the chargeback is necessary, whether to automatically represent the disputed payment vehicle transaction, or whether to automatically accept financial liability for the disputed payment vehicle transaction. Additionally, the chargeback processing server automatically collects representment evidence in response to determining to automatically represent the disputed payment vehicle transaction. Other embodiments are described and claimed.