EU digital regulation has created barriers to competitiveness in transport and beyond. It has created complexity, a high compliance burden and cost, fragmentation, legal uncertainty and unbalanced interpretations, damaging the digitalisation of transport. The number of regulations is too high, creating complexity, overlaps and incoherences. The combination of principles-based regulation, intended to provide flexibility, and very high fines has resulted in the “principles paradox”: regulated entities playing it conservative to avoid fines, damaging innovation. The principle of accountability imposes a high compliance burden. Finally, a “mandate bias” can be identified as single-purpose regulators tend to overweight their mission (privacy, security, etc.) over other values and even fundamental rights such as free enterprise. Case studies are provided. The paper lastly outlines ten measures to lessen compliance burdens, enhance legal certainty, and strengthen competitiveness.