Contrary to its predecessor, the new regulation does not provide for a specific exemption from the screening of the diplomatic bag. As there is no uniform practice in that regard within the Union, Member States are trying to square the circle in the Council’s International Law Working Party by exploring various ways of implementation. The unquestionable right of States to have the contents of their diplomatic communications protected and a more recent but obviously valid concern over the security of air transport are apparently in conflict with each other. How to mitigate such collision by way of a dynamic interpretation of the half-century old Vienna Convention on Diplomatic Relations? This article is an analysis of the relevant international legal instruments and the existing practice with a view to putting possible solutions on the table.