The Bangladesh Labour Act 2006 establishes a foundational binary: employees classified as “workers” attract the full suite of statutory protections, while those categorized as “managerial employees” do not. This definitional divide, though doctrinally defensible, has become a vector for systematic exploitation. Organizations across Bangladesh, spanning the private sector, state-linked enterprises, and commercial banks, routinely assign inflated designations to otherwise ordinary employees, thereby avoiding liability under the Act and depriving employees of fundamental entitlements including overtime pay, termination benefits, and access to labour courts. The judiciary has consistently emphasized that substance must prevail over title, holding that the nature and scope of actual functions determine an employee’s legal status. However, in the absence of a structured statutory framework, judicial responses remain reactive and case-specific, offering limited systemic protection. This article examines the legal framework, patterns of misclassification, and judicial responses in Bangladesh, and compares them with the approach adopted under Singapore’s Employment Act. It proposes doctrinal reforms and clearer ex ante guidance to reduce abuse and enhance legal certainty.