Background: The new training allowance policy has been put in the Social Insurance Institution to bring back to employment workers with health problems unfit for their previous occupation. These people, following specific vocational training, may acquire new skills and competencies to stay on the labor market. The aim of this study was to assess the role of the Social Insurance Institution in the activation of persons with health problems, which was carried out by issuing opinions about the appropriateness of vocational retraining. Material and Methods: The analysis included 460 cases in which decisions on the appropriateness of vocational retraining, due to the inability to work in the current profession, were issued in 2009. Results: It was found that 40.9% of the analyzed cases were not in accordance with the principles of adjudicating on the incapacity for work and applicable law. The majority of the study group (72.4%) were people with basic vocational education. No significant changes were found as regards gender, age and the place of residence between the retrained (N = 89) and not retrained subjects (N = 252). In the retrained group including 89 persons, 13 subjects started to collect pension again within 6 months; and 1 person collected pension while working. In addition, 51 (57.3%) retrained subjects were unemployed. After 12 months, the number of unemployed subjects decreased to 31. Conclusions: The effectiveness of the training allowance as a tool for the activation of people with health problems, expressed as the number of retrained people who returned to the labor market, is low. More than 80% of the people fail to get retrained and some of them again submit pension applications. A large number of incorrect vocational retraining opinions, as well as the lack of cooperation between institutions conducting retraining (the Social Insurance Institution and labor offices) resulted in a limited effectiveness of the training allowance. In order to enhance the effectiveness of the training allowance, it is necessary to carry out organizational and legislative changes, with particular emphasis on expanding the knowledge of medical examiners representing the Social Insurance Institution and occupational health physicians, as well as to improve cooperation between all institutions involved in the occupational activation of people with health problems. Med Pr. 2020;71(3):309–23