Some of the loudest calls for reform in post-revolutionary Iran have come from those closest to the regime. President Mohammad Khatami (1997–2005) and President Hassan Rouhani (2013–) were key players in Ayatollah Khomeini’s Iran, but were both later elected to the presidency on reform platforms. This chapter evaluates President Rouhani’s track record in instituting freedom-on-the-internet reforms in Iran, to understand the efficacy of the ‘inside-track’ approach to human rights change. Using Kingdon’s Multiple Streams Theory of Change, the analysis shows that while Rouhani enjoyed a wide ‘policy window’ to enact reforms in relation to Iran’s economy—including resolving the nuclear issue—he enjoyed no such popular mandate on human rights reform. In this regard, Rouhani’s progress on improving internet freedom has been limited. Mobilising the ‘inside track’ is not a guaranteed pathway to human rights-based reform in Iran.