The study reported in this paper examined a group of Australian taxpayers who have expressed a preference for a creative and aggressive tax agent. The study attempted to understand how high-risk taxpayers and high-risk practitioners form their partnerships by examining aggressive taxpayers' attitudes and perceptions of the Australian tax system. Data were taken from 2040 Australian taxpayers who had responded to a national survey on tax issues. Results from a series of independent sample t-tests revealed that there are a number of important differences between 'aggressive' and 'non-aggressive' taxpayers. Finally, a logistic regression analysis was used to determine which variables most effectively differentiated aggressive taxpayers from non-aggressive taxpayers. The findings are discussed in a regulatory context and possible solutions for how tax authorities might deal with this high-risk group of taxpayer are suggested.