Technology has fundamentally changed work including where it happens, how people collaborate, and how people hire and pay workers. This contribution discusses the implications of these changes for classic tax questions, such as jurisdiction, expenses, worker classification, and tax reporting. Beyond these tax issues, this contribution offers two broad warnings. First, tax regimes should be wary of treating people more like businesses and less like workers of old. Second, despite a long tradition of social safety nets in many jurisdictions across the world, the pandemic created a new and rapid need to assist disrupted workers – and in some countries the tax system proved critical in facilitating a government response. Such an option is available to governments only if the tax administration is sufficiently healthy. Accordingly, jurisdictions must invest in the tax administration infrastructure, not just for regular operations with taxpayers, but for moments of crisis as well. Finally, this paper identifies broader cautions for tax systems in the coming decades.