This article is an attempt to deepen the knowledge about the relationships between Machiavellianism and the search for and experience of a sense of the meaning in life in penitentiary recidivists. The study emphasises the role of this knowledge in penitentiary interactions. The significance of Machiavellianism for penitentiary studies is conditioned by the fact that this construct captures the essence of the attitudes and beliefs illustrating the relation of individuals to the social world. Moreover, the significance of the problem of searching for and experiencing the meaning in life in relation to the area of penitentiary social rehabilitation is conditioned by the issue of linking these constructs with the aspect of positive change and achieving general adaptation. The study indicates a number of theoretical and empirical premises justifying the occurrence of direct relationships between the area of Machiavellianism and the sphere of existential experiences. The research objective was formulated based these assumptions and concerned the determination of the relationship between Machiavellianism and the meaning of life in repeatedly incarcerated convicts. A group of 59 penitentiary recidivists (aged 27 to 68; M = 39.75, SD = 8.84) was tested using the Machiavellian scale (Mach IV) and the Meaning in Life Questionnaire (MLQ), which enabled the measurement of the search for and presence of meaning in life. The relationships between the variables were determined by correlation. The analyses showed the existence of numerous significant relationships between the Machiavellian syndrome and the search for and presence of meaning in life. A greater overall level of Machiavellianism was associated with a lower intensity of the search for and the presence of meaning in life. The obtained results have implications for penitentiary practice with regards to influencing convicted recidivists. In light of the acquired results, it is justified to include educational and psycho-corrective elements that undermine Machiavellian beliefs, which is a factor supporting the orientation towards the search for meaning in life and has potential to create meaning.