This practical checklist is designed for HR teams, legal departments, and hiring managers who need to ensure that their independent contractor engagements are compliant with local regulations in every jurisdiction where they operate. Contractor misclassification carries serious financial and legal consequences, and the rules governing worker classification vary significantly from country to country. The checklist is organized into three phases. The pre-engagement phase covers the initial classification assessment: evaluating the nature of the work, the degree of control you will exercise, the contractor's economic independence, and the specific classification tests that apply in the contractor's jurisdiction. We provide a standardized assessment template that maps the most common factors across major jurisdictions, helping you identify high-risk engagements before contracts are signed. The engagement phase covers contract requirements, including the essential clauses that must be present in contractor agreements to support independent contractor status, as well as invoicing and payment structures that align with contractor classification. The ongoing monitoring phase is where many companies fall short. Contractor relationships evolve over time, and an arrangement that started as a clearly independent engagement can gradually shift toward an employment-like relationship through scope expansion, exclusivity, integration into company operations, or extended duration. The checklist provides a quarterly review framework that reassesses classification risk based on how the relationship has developed, with clear escalation triggers and remediation steps when risk levels change.