This article investigates the political legitimacy of the health care system and the effects of austerity on the population’s welfare, paying particular attention to Portugal, a country severely harmed by the economic crisis. Based on analysis of data collected from the European Social Survey on 14,988 individuals living in private households during the years between 2002 and 2018, the findings of this study aim to analyze the social and political perception of citizens on the state of health services in two distinctive periods—before and after the economic crisis, according to self-interest, ideological preferences, and institutional setup as predictors of the satisfaction with the health system. The results demonstrate a negative attitude towards the health system over the years, a consistent drop during the financial crisis period, and a rapid recovery afterward. The research also shows that healthcare evaluations depend on the perceived institutional effectiveness in the citizenry’s eyes. The more the citizens perceive the government as effective and trust-worthy, the more they are satisfied with the health system. Also, differences in healthcare evaluations among social groups were felt unequally: while vulnerable citizens were more affected by the Government’s plan of austerity measures for health reform, healthcare evaluations of better-off social groups—younger individuals, those with higher incomes, higher education, and better health status—did not decline. This study contributes to the academic debate on the effects of austerity on the population’s welfare attitudes and highlights the need to examine the different impacts of reforms introduced by the crisis on social groups.