Ethical tax lawyering is about more than knowing the outer boundaries imposed by the rules of ethics and standards of tax practice. It is also about how to make difficult discretionary decisions within those boundaries. This talk will discuss different models of tax advising that can help tax lawyers make those discretionary decisions in a way that is consistent with the lawyer’s sense of ethics, even when providing advice for aggressive tax planning. In addition, this talk will discuss threats that hinder a lawyer’s ability to implement their preferred approach to tax advising. These threats include bounded ethicality, which is the idea that internal (e.g., psychological) and external (e.g., organizational) pressures can lead people to engage in ethically questionable behavior inconsistent with their preferences. This talk will then discuss several strategies that can help prevent lawyers from succumbing to these threats and crossing lines they do not want to cross.