Anonymous communication systems ensure that correspondence between senders and receivers cannot be inferred with certainty. However, when patterns are persistent, observations from anonymous communication systems enable the reconstruction of user behavioral profiles. Protection against profiling can be enhanced by adding dummy messages, generated by users or by the anonymity provider, to the communication. In this work we study the limits of the protection provided by this countermeasure. We propose an analysis methodology based on solving a least squares problem that permits to characterize the adversary’s profiling error with respect to the user behavior, the anonymity provider behavior, and the dummy strategy. Focusing on the particular case of a timed pool mix we show how, given a privacy target, the performance analysis can be used to design optimal dummy strategies to protect this objective.