This chapter analyzes the legal framework of lawful interceptions by Law Enforcement Agencies (LEAs) in the EU. Firstly, it describes it as an exception to the principle of confidentiality of electronic private communications and presents the democratic safeguards attached to its regime. Subsequently, it discusses the present crisis of lawful interception in the digital era, highlighting weaknesses in both the practical and theoretical frameworks. It demonstrates that the currently advanced tools used by the LEAs to circumvent cryptographic protection exist within a legal grey area. Lastly, it delves into the rise of the concept of a “serious offense” as an additional democratic safeguard for the regime. The chapter argues that this concept is inherently flawed and that other democratic safeguards, such as the generalization of information about the data subject at the conclusion of the interception, should be considered instead.