This study examines the effect that legislation on insult and defamation has on media practitioners and artists in Zimbabwe. The results of the study are based on analysis of data gathered through interviews with Zimbabwean journalists, editors, artists and scholars in March/April 2014. I look at factors that have an impact on the deterring effect of legislation and apply these theories to the data from Zimbabwe. The study documents that the media and art practitioners in Zimbabwe have multiple strategies to cope with the restrictive legislation, such as self-censorship, anonymity, the use of metaphors or multi-layered communication, and anonymous online publications. These strategies indicate that the legislation has an effect. I have also applied theories on deterring factors of legislation in my analysis. A law or rule is most effective when the law is known; the perceived costs are greater than the benefits, and there is a high perceived risk of detection of the violation. All of these factors are present in Zimbabwe, making the legislation more deterring on public expressions by the media and artists. I have also looked at the ability and willingness of the potential offender to act rationally and not violate the law. Here I have shown that there is in fact a high willingness among media practitioners to violate this legislation, which is considered illegitimate and unconstitutional. This indicates reduced effectiveness of the legislation. However, I also show that practices such as immediate detention, the use of violence or threats of violence, and the lack of trust in the government s willingness to abide by the law, increases the deterring effect of the legislation.