Advances in the automated detection of offensive Internet postings make this mechanism very attractive to social media companies, who are increasingly under pressure to monitor and action activity on their sites. However, these advances also have important implications as a threat to the fundamental right of free expression. In this article, we analyze which Twitter posts could actually be deemed offenses under German criminal law. German law follows the deductive method of the Roman law tradition based on abstract rules as opposed to the inductive reasoning in Anglo-American common law systems. This allows us to show how legal conclusions can be reached and implemented without relying on existing court decisions. We present a data annotation schema, consisting of a series of binary decisions, for determining whether a specific post would constitute a criminal offense. This schema serves as a step towards an inexpensive creation of a sufficient amount of data for an automated classification. We find that the majority of posts deemed offensive actually do not constitute a criminal offense and still contribute to public discourse. Furthermore, laymen can provide sufficiently reliable data to an expert reference but are, for instance, more lenient in the interpretation of what constitutes a disparaging statement.