While research on translation technologies has long focused on interlingual transfer, the rise of plain language and easy-to-read practices, together with the rapid spread of generative AI, has highlighted the increasing importance of intralingual translation. FLO (Facile da Leggere Online), a digital assistant for Italian, supports text simplification by combining linguistic rules, lexical resources, and artificial intelligence, including generative models, to guide authors in producing accessible texts. Rather than fully automating rewriting, FLO flags issues, suggests alternatives, and explains choices, thereby guiding users in their writing process. The article examines FLO’s design, technical architecture, and pedagogical dimension, with particular attention to issues such as synonymy management, lexical choice, and the balance between automation and human supervision. It shows that FLO promotes clearer documents while fostering user training and metalinguistic awareness, illustrating how AI-inspired tools can reinforce the right to information by advancing accessibility, participation, and transparency in institutional and professional communication.