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This paper opens with a brief backstory of the contradictory elements surrounding the first Bachelet election, then juxtaposes the accomplishments of both Bachelet administrations against the odds in place to give emphasis by comparison. The backstory serves as a segue into the discussion about a notable change in the Chilean electorate between Bachelet's first term (2006–2010), when her exit approval rating reached an unprecedented 84%, and her second (2014–2018), when it suffered a record low 26%. In the face of multiple reforms, many of them passed during the second term, what explains the chronic dissatisfaction with political performance on the part of the Chilean populace? A discussion of the altered political landscape explores the role of cyber actors (social media) in citizen engagement and its impact on political processes in the twenty-first century. The perspectives offered have relevance not only for the Chilean context but also for contexts across the globe, both in developing and developed nations.