Michele Bachelet, Chile’s first female president, was elected in 2006 with an explicit gender agenda, promising to appoint new faces (including women) and implement some positive gender change. After a period heading UN Women, she was subsequently reelected for a second term in 2013 with a decisive majority. This paper focuses on Bachelet’s efforts to introduce progressive measures and the constraints that she has faced in a context where both formal and informal political institutions could act as barriers to change. It will provide a gendered analysis of both Bachelet’s first period in government together with her campaign for re-election in 2013 and the first 100 days of her second presidency in which the reform agenda for her second term was introduced. This will allow a systematic reassessment of both the achievements and challenges of her first term as well as an analysis of the major challenges that she will face her during her second term. Using a feminist institutionalist approach, the paper locates Michelle Bachelet’s presidencies within the wider debates about reform and institutional change and particularly efforts to realize gender equality goals.