This paper discusses various legal challenges of the “digitisation of the single market”. The question arises to which extent the current regulatory framework appears suitable to deal with the presented challenges of digitisation and where additional regulation is required. In the field of autonomous decision-making by AI, we identified the most pressing need for new regulation. While the EU (and increasingly Austria, as well) is aware of this need, regulation to date remains scarce. Though the EU legislator has already taken specific precautions for the use of algorithms in the GDPR, such regulatory approaches are missing in most other fields of law. In contrast to this, antitrust law and product liability law already appear to be well suited to meet the challenges posed by digitisation. This is especially true for product liability law, which is in principle apt to cover the specific challenges of the convergence of software and hardware in smart products. However, uncertainty about its applicability to incorporeal goods would make clarification of current product liability legislation advisable – a view shared by the European Commission. Two more fields very recently received some legislative attention due to the changing needs of a digital society: the postal sector on the one hand, and e-government on the other hand. In both fields, new legislation – tellingly in the form of (partially) directly applicable regulations – has recently been passed by the EU – a sharp contrast to the case of self-learning AI. However, while the integration of the new regulation on cross-border parcel delivery will probably not pose major challenges for domestic markets, the implementation of the Single Digital Gateway will raise serious organisational and legal challenges for national administrations (especially when taking into account the limited success of the previous related initiative on the points of single contact under the Services Directive).