The main purpose of detention in a modern, humanitarian prison system is to bring the prisoners to live in a free society in a manner consistent with applicable laws and morals. The indicators of modernity are also ways and means by which attempts are made to achieve this goal. In many European and non-European prisons, physical culture achievements are commonly used in working with prisoners. They organize programmed resocialization activities for prisoners with a substantial share of physical education and recreational free time activities. Sometimes, prisoners are offered the chance to take their own initiatives to encourage healthy lifestyles. In addition to teaching, during which the prisoners participate in physical activity, they use interaction with sports authorities in the form of discussion meetings between prisoners and athletes. Such meetings are also organized at the House of Detention in Inowrocław, which operates a half-open unit for the convicts. These meetings are the part of the activities of “Paragraph”, the Olympian club (based at the Inowrocław prison) subject to the Polish Olympic Committee. The author participated in several such meetings as an invited guest or co-organizer and observed that they are primarily of a recollective character. But it was hard to find in them specific, praxeologically structured and conceptually implemented resocialization interactions. Teleological vagueness initiated the search for the real purpose of these meetings by means of observation. The meetings clearly appeared to have more of an ad hoc (referring to the conditions in prison) than a prospective character (undertaken with a view to the period after release). These findings were the inspiration for the development of the main objectives of a two-step strategy of a change in scenarios of the meetings between the convicts and athletes, the ultimate goal of which was to give them the characteristics of programmed rehabilitation. They defined the procedure for involving sportsmen to accomplish the objectives in the area of mental health and social development and made the selection and development of tools to measure the effects of these interactions. The article is a report on research designed to determine differences in perception of health, as well as on conducting health activities among those inmates who participated in the program “Active today, different tomorrow” and those who did not participate in it. The study involved 67 penitentiary recidivists. Two questionnaires by Siegfried Juczyński were used: the List of Health Criteria and Health Behaviour Inventory. The results gave the possibility to formulate important methodological implications for practitioners who involve prominent sportsmen in resocialization. They also proved useful in efforts to create another resocialization program that uses sports activity in resocialization.