What is the difference between illegal hate speech, and legal hate speech? How free is the freedom of expression, and what are its thresholds? Can, and if so, how could technology help guarding these thresholds of what is freedom of expression, and what is not? How to arrange for more transparency by digital media platforms so their ways of acting or not acting to protect the freedom of expression can be monitored? What kind of transparency would one need, to cater for a higher level of accountability of the various stakeholders? How to arrange for that beyond national or regional jurisdictions, in a global perspective? What is the role of individuals and organisations? Are they aware and empowered sufficiently? These and other key topics are addressed in this Dialogue with Guilherme Canela, Chief of Section – Freedom of Expression and Journalist Safety at UNESCO.