This article aims to provide an analytical framework for the legal design of experimental legislation in the field of technology and governance. The article focuses on ‘legally disruptive experiments’, either as concretizations of factual or legal acts. The relations between such experiments and various basic types of (non) experimental legislative arrangements are mapped. The scope for experimenting is defined in terms of legal liberty and ability space, on the basis of normative positions within either rules of conduct or rules of power. A distinction is suggested between three scopes of permissiveness to (i.e., as freedom, full and partial permissiveness), and five types of permissive norms (i.e., mere silence, eloquent silence, with toleration, with rights, and with enabling rights) – all of which are potentially relevant to experimentation. Departing from the idea of legal disruption, the article goes on to focus on exceptional permissiveness to experiment by temporary derogation. Such exceptions can be arranged through limiting an obligatory legal norm upon a ‘subset’ scope of application, defined by operative facts or by legal acts. The use of these mechanisms can lead to two possible groups of exceptional, derogative regimes for experimentation (‘Permissiveness v. Obligations’ and ‘Permissiveness v. Permissiveness’), encompassing five arrangements (in short: legislative permissiveness over obligations; unlegislated permissiveness over obligations; strong silent permissiveness over weak silent permissiveness; legislated permissiveness over unlegislated permissiveness; broad over narrow permissiveness), each of which can come (as regulatory holidays or sunset clauses) with combinations of no, some or many reservations and facilitations.