Nowadays, advanced security mechanisms exist to protect data, systems, and networks. Most of these mechanisms are effective, and security experts can handle them to achieve a sufficient level of security for any given system. However, most of these systems have not been designed with focus on good usability for the average end user. Today, the average end user often struggles with understanding and using security mecha-nisms. Other security mechanisms are simply annoying for end users. As the overall security of any system is only as strong as the weakest link in this system, bad usability of IT security mechanisms may result in operating errors, resulting in inse-cure systems. Buying decisions of end users may be affected by the usability of security mechanisms. Hence, software provid-ers may decide to better have no security mechanism then one with a bad usability. Usability of IT security mechanisms is one of the most underestimated properties of applications and sys-tems. Even IT security itself is often only an afterthought. Hence, usability of security mechanisms is often the after-thought of an afterthought. This paper presents some guide-lines that should help software developers to improve end user usability of security-related mechanisms, and analyzes com-mon applications based on these guidelines. Based on these guidelines, the usability of email encryption is analyzed and an email encryption solution with increased usability is presented. The approach is based on an automated key and trust man-agement. The compliance of the proposed email encryption solution with the presented guidelines for usable security mechanisms is evaluated.