The European Convention guarantees the right to assembly. Since the ratification of the Convention Sweden has been obligated to make proportionality balances when granting or restricting the right. However, the process of how the proportionality assessments work when cancelling or dissipating a public gathering, and thereby limit the right to protest, is unmapped. Therefore, the aim of this study is to analyze the legal problems that emerges by studying the Parliamentary Ombudsman’s and the Chancellor of Justice’s proportionality assessments relating to the right to protest. This will be done by comparing nine decisions made by the Parliamentary Ombudsman and the Chancellor of Justice between 1995 and today (2017).   The study concludes that the Parliamentary Ombudsman and the Chancellor of Justice overall made proportionality assessments and thereby respected the principle of proportionality. However, some legal problems complicated the assessments. The definition of resolution, public gathering and severe disorder can differ, which can result in discretional exercise of official authority. This may, in turn, restrict the freedom of assembly and thereby be a threat to the democracy.