It is often suggested in the literature that employees regard technical security measures (TSMs) as user-unfriendly, indicating a trade-off between security and usability. However, there is little empirical evidence of such a trade-off, nor about the strength of the associated negative correlation and the importance employees attach to both properties. This paper intends to fill these knowledge gaps by studying employees’ trade-offs concerning the usability and security of TSMs within a discrete choice experiment (DCE) framework. In our DCE, employees are asked to indicate the most preferred security packages that describe combinations of TSMs. In addition, security and usability perceptions of the security packages are explicitly measured and modelled. The models estimated from these observed responses indicate how each TSM affects perceived security, perceived usability and preference. The paper further illustrates how the modelling results can be applied to design highly secure packages that are still preferred by employees. The paper also makes a methodological contribution to the literature by introducing discrete choice experiments to the field of information security.@en