We study the problem of k-anonymization of mail messages in the realistic scenario of auditing mail traffic in a major commercial Web mail service. Mail auditing is necessary in various Web mail debugging and quality assurance activities, such as anti-spam or the qualitative evaluation of novel mail features. It is conducted by trained professionals, often referred to as "auditors", who are shown messages that could expose personally identifiable information. We address here the challenge of k-anonymizing such messages, focusing on machine generated mail messages that represent more than 90% of today's mail traffic. We introduce a novel message signature Mail-Hash, specifically tailored to identifying structurally-similar messages, which allows us to put such messages in a same equivalence class. We then define a process that generates, for each class, masked mail samples that can be shown to auditors, while guaranteeing the k-anonymity of users. The productivity of auditors is measured by the amount of non-hidden mail content they can see every day, while considering normal working conditions, which set a limit to the number of mail samples they can review. In addition, we consider k-anonymity over time since, by definition of k-anonymity, every new release places additional constraints on the assignment of samples. We describe in details the results we obtained over actual Yahoo mail traffic, and thus demonstrate that our methods are feasible at Web mail scale. Given the constantly growing concern of users over their email being scanned by others, we argue that it is critical to devise such algorithms that guarantee k-anonymity, and implement associated processes in order to restore the trust of mail users.