While information technologies present organizations with opportunities to become more competitive, unsettled social norms and lagging legislation guiding the use of these technologies present organizations and individuals with ethical dilemmas. This paper presents two studies investigating the relationship between intellectual property and privacy attitudes, Machiavellianism and Ethical Ideology, and working in R&D and computer literacy in the form of programming experience. In Study 1, Machiavellians believed it was more acceptable to ignore the intellectual property and privacy rights of others. Programmers and R&D workers considered violating intellectual property rights more acceptable. Programmers did not consider violating privacy rights more acceptable, but R&D workers did. Finally, there was an interaction between Machiavellianism, programming and R&D. Machiavellians who also had programming experience or worked in R&D found violations of intellectual property much more acceptable. The effect of Machiavellianism on attitudes toward violations of privacy was enhanced by working in R&D, but not by programming experience. In Study 2, idealists believed it was less acceptable to ignore the intellectual property and privacy rights of others. Relativists found it more acceptable to violate intellectual property rights, though they did not consider it more acceptable to violate privacy rights. Those with programming experience were more accepting of intellectual property rights violations, but not of privacy violations. Finally, programming experience moderated the relationship between idealism, relativism and attitudes toward these unethical information practices. Implications for diminishing unethical behavior among Machiavellians, Relativists, programmers and those in R&D are discussed.