The problems surrounding complexity as a pervasive feature of the systems and laws through which citizens are governed are well known. Complex laws and processes are likely to be difficult for many people to understand, creating problems for both compliance and enforcement of rights. There are also potential difficulties for administrative authorities, since they may struggle to meet a legitimating goal of applying rules accurately. Rule complexity may weaken the law’s legitimacy. Complexity also tends to generate economic burdens. The perception of complexity as problematic has prompted a number of national and international simplification initiatives. They aim to counter complexity either by managing it better (for example, through IT systems) or reducing it. Some, like the EU’s Better Regulation initiative, favour changes to the legislative frameworks through codification or the removal of duplication, inconsistencies and obsolete provisions. Others look to structural features of law-based systems, making changes designed to streamline the governing legal and administrative frameworks, as in the UK’s present welfare reforms, to make systems easier and less costly to operate. In my presentation I consider how far the measurement of complexity is possible and question whether, if it is not, the realisation of simplification can be empirically assessed. Also, according to complexity theory, an important feature of complex systems is the unpredictability of some of the interactions within them, so I will question how far it is possible to guarantee the realisation of the intended outcome of simplification reforms. A further issue is whether complexity is always undesirable; from a legal perspective, there is a question as to whether simpler laws may enhance or weaken individual rights. Where public law and regulation are concerned, should we, at a political level, pay more attention to the potential dangers of simplification as a means to removing or limiting entitlements or freedoms of the individual?