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This paper aims to present concrete and verified guidelines for enhancing the usability and security of software that delegates security decisions to lay users and captures these user decisions as a security policy.

This work is an exploratory study. The authors hypothesised that existing tools for runtime set‐up of security policies are not sufficient. As this proved true, as shown in earlier work, they apply usability engineering with user studies to advance the state‐of‐the‐art.

Little effort has been spent on how security policies can be set up by the lay users for whom they are intended. This work identifies what users want and need for a successful runtime set‐up of security policies.

Concrete and verified guidelines are provided for designers who are faced with the task of delegating security decisions to lay users.

The devised guidelines focus specifically on the set‐up of runtime security policies and therefore on the design of alert windows.

Electronic commerce has recently shown enormous potential to take over a significant share of the sales market. There is a need to provide services that can reach individual computer users with different information profiles and levels of expertise. In this article the concept of Web assistants, human assistants working in an electronic Web shop, is presented. This human‐computer collaboration provides intelligent and adaptive services via an integrated communication media. A prototype of a Web assistant system has been implemented. While browsing through the system the user can call for human assistance should the need arise. Presents the results of a usability study performed on the prototype system. Recent commercial moves in the direction discussed in this article increase the importance of the usability study. The results are encouraging, especially when it comes to the attitude aspects of usability. The subjects were extremely enthusiastic about the concept of Web assistants and its implications. The human Web assistant who participated in the field trial highlighted the importance of user modelling. Although the system is mainly in the context of electronic commerce, it can be used in many other contexts. These include home automation, digital libraries, and technical support, to name a few.