Aggressive tax planning is found to be a cyclical phenomenon in Australia and the United States. While people strongly disapprove of it, mass participation in aggressive tax planning occurs during cyclical upswings, probably at a level involving well over 100,000 Australians in illegal schemes during the late 1990s. We analyse these cycles as a market in the vice of tax scheme promotion that is countered by widespread virtuous sentiments in the democracy. Community attitudes to tax cheating are therefore not seen as the problem, but as crucial to its solution. There is a democratic demand for tax system integrity. This demand creates a market for honest tax advice professionalism. Sophisticated regulators can use these community attitudes as the crucial resource for flipping markets in vice to markets in virtue. Cycles occur because markets in virtue and vice dominate at different periods of history.