This chapter continues the analysis of anonymity and transparency, focusing on the socio-technical concepts of obfuscation and traceability. It heeds the impact of anonymity-enhancing strategies applied by different actors, and of investigative analytics tools. It shows how crypto-assets can be deployed in the laundering process in multiple ways, and how this hampers both identification and the relevant categorisation of risks. Relatedly, it focuses on red flag indicators by the FATF, phrased without a clear separation between the ways in which anonymity can be enhanced. The chapter argues for deploying a teleological methodology when evaluating the meaning of features such as anonymity—i.e., considering the context, composed by the crypto-asset space and the AML/CFT framework. Meanwhile, it suggests the identification of specific benchmarks to differentiate between the various degrees of anonymity enshrined by different crypto-asset ecosystems without running into the risk of overfitting. It is in this context that the concept of accountability, ensured by the auditability of relevant transactions, emerges as pivotal.