Two comprehensive municipal structural reforms have been implemented in Iceland, the first one starting in 1991 and ending in 1993, and the second one starting in 2003 and ending in 2005. Other reform intentions by governments and ministers have been planned but have not come to be a reform. The aim of this article is to identify the reform strategies used, the conflicts that arose, the outcomes of the reforms and how strategies, conflicts and outcomes are connected. Baldersheim and Rose’s (2010) framework on how territorial reform strategies can shape conflicts that arise, as well as the outcomes of the reforms will be used in the analysis of these two structural reforms. The analysis is based on secondary data from government reports, official data on municipal referendums, a 1994 survey, and an evaluation report. The main finding is that both these reforms were top-down-oriented, which contributed to strong resistance, especially in small and peripheral municipalities. Both reforms reached their peak in referendums, which were not successful at all, primarily because the people in small municipalities voted against amalgamation. In both reforms, the Icelandic Association of Local Authorities supported the government’s top-down approach to implement comprehensive amalgamation reforms, while most of the smaller member municipalities opposed amalgamation. The article explains how the Association’s internal structure has created this paradox. Despite very limited success in the 1993 and 2005 referendums, the aftermath of the 1993 referendum shows that the effort to try to convince small municipalities to amalgamate indirectly led to an avalanche of voluntary bottom-up oriented amalgamations between 1994 and 2002, where the number of municipalities went down from 196 to 105.