Entering the 2020s, Bolivia faces the challenge of driving post-Covid-19 economic recovery and charting a sustainable path towards inclusive development. One of the keys to recovery are public resources based on a more equitable tax system and a wider tax base. Between 2005 and 2015, as a result of high commodity prices, revenues from gas provided burgeoning public funds and created an illusion of abundance, which put off the need for tax reform, most likely lowered taxpayer morale, and stymied institutions' ability to scale up tax collection. This chapter analyzes some of the political tensions of tax reforms aimed at improving tax collection in a context of dependency on hydrocarbon revenues. The analysis centers on the Bolivian tax system, addressing the importance of hydrocarbon revenues for the public sector's revenue and its redistributive character. Additionally, through the identification of actors and sectoral interests and of the political economy inherited from past reforms, this chapter explores the political possibilities and limitations of actions aimed towards improving tax effectiveness and progressivity.