This paper focuses on the automatic annotation of linguistic readability features in institutional Italian texts. Specifically, our research deals with qualitative linguistic features identified by other researchers as elements of complexity. Italian administrative texts often exhibit an excessive complexity that interferes with citizens’ right to access information. Many authors identified the features responsible for low readability and proposed rewriting rules. We will focus our research on complex prepositions and conjunctions, passive voice, nominalizations, support verb constructions, and double negation. Specifically, we developed an automatic readability assessment tool that identifies these readability issues in sentences, through NooJ dictionaries and grammars. Finally, we applied it to a corpus of institutional texts.