Background: A rise in pharmaceutical expenses in Portugal led to the introduction of policy measures aimed at controlling outpatient public costs. This research examines and categorizes the most common pharmaceutical measures implemented during the Troika intervention, as well as comparing this period of time to prior ones. Methods: A hierarchical structure of descriptors was built to classify and group measures over a 20-year period, including whether they might be deemed austerity measures. The nature, relative weight, and frequency of measures, along with the evolution of public drug expenditure, were assessed. Results: Although there were fluctuations, frequency tended to increase. The highest number of policy changes per year was in 2010, a year before the financial assistance. The Troika intervention was characterized by a strong emphasis on pricing and prescription-related initiatives. Generic medicines played a significant role in the effort to reduce public drug expenditure. Conclusions: During the Troika intervention, outpatient public drug expenditure was consistently reduced through a comprehensive “package of measures” aimed at both the demand and supply sides. The effectiveness of some previous independent measures, if any, was temporary.