With the advent of mobile application-based aggregator models, engaging stakeholders has become more challenging as the lines separating external and internal customer are blurred. This study deciphers the points of engagement and points of disengagement for the major stakeholders viz. drivers and commuters for the cab aggregators in India. Through semi-structured interviews of cab drivers and triangulation through media reports, interviews of customers, bank officers and regional transport officers, the authors elicit what enhances customer and driver engagement and what reduces it. Results show that technology has a dual nature where it enhances as well as diminish the engagement of drivers. The identity of a professional and the flexibility offered by this app-based work fosters engagement for drivers as well as customers. Changes in organizational and government norms are a source of disengagement. The theoretical and practical implications are also discussed. Copyright © 2020, IGI Global.