This article explores the influence of behavioural monitoring through telematics on individual risk classification within the insurance sector. By synthesizing empirical findings and theoretical constructs from behavioural economics, criminology, and information systems, we examine how continuous surveillance modifies driving behaviour, enhances risk assessment, and alters consumer and organizational incentives. Drawing upon extensive literature, we discuss the monitoring effect's implications on behaviour modification, moral hazard, and market efficiency. Evidence from in-vehicle monitoring systems, peer influences, and privacy concerns provides a holistic view of the evolving risk landscape in telematics-adopting insurance frameworks.