Digital service systems are changing the world as we know it, enabling companies to embrace new forms of relationship with their customers. The aim of this article is to propose a categorization of service failures in digital service systems and an illustration of recovery solutions based on life situations. Thus, this article used an exploratory case study research conducted in a Portuguese private bank. Data collection involved multiple sources, such as semistructured interviews, customer complaints from an online database, and direct observation. The case revealed that digital service systems are not failure proof and service failures are inevitable. As a result, companies are struggling to consistently maintain high service standards across all channels and, for that purpose, have essentially invested on automated interactions. On the other hand, humanized recovery solutions are expected to enable organizations to make significant progress, including prevention and corrective actions, that will mitigate the perception of poor service delivery. While current studies tend to focus on what is going wrong in digital engagement, researchers have hitherto not investigated sufficiently this digital breakdown and the subsequent recovery solutions.