The debate on job quality in worker cooperative is characterised by two different poles. Some contributions tend to focus on job satisfaction and intrinsic dimensions of job quality, highlighting how they are generally higher in cooperatives compared to capitalist firms because of their democratic character which translates into a peculiar organisational and managerial ethos. Other contributions, based on “harder” measures of job quality, show that cooperatives perform slightly better than capitalist firms, but their job quality is at risk of “deterioration” due to market pressures. Through a qualitative analysis of job quality in some of the sectors of the Italian economy in which the incidence of cooperatives on total employment is highest (social services, cleaning, and meat processing) based on semi-structured interviews with workers and relevant experts (trade unionists, managers, clients), this paper wants to make two points regarding this debate. Looking at hard indicators of job quality, the paper highlights that worker cooperatives in Italy often perform worse than other companies active in the same sector. This is connected to the fact that differentials in labour regulation and employment relations constitute a key factor explaining why this form of enterprise was able to expand in the analysed sectors. Thus, we argue that cooperatives have acted as institutional loopholes through which regulation could be circumvented and labour costs reduced, negatively affecting job quality and opening up to a significant redefinition of employment relations in the four sectors.