A critical issue for tax and regulatory compliance is determining a worker’s status as an employee, independent contractor or something else. This issue has been the subject of recent litigation and given the rise of the gig economy is likely to become more acute as more people are given the ability to undertake entrepreneurial activities. This article will explore the current issues that concern “worker status” and some of the recent case law, as well as the potential influences this distinction can have on the worker, the engaging entity, government agencies and society as a whole. A number of recommendations are formulated in terms of systems administered by the tax office as a possible way to provide greater certainty, knowledge and equity in this area.