Companies implement technical security measures to let their employees behave in a secure manner. Employees however, can circumvent these measures. To solve this circumventing problem companies should know better what the preferences of their employees are. Employees’ preferences with regards to technical security measures are based on the perceptions of usability and security and the trade-off between these aspects. With the help of perception based choice modelling applied on a survey distributed among employees, this research aims to give insight into these perceptions and trade-off. This research reveals that the effect of multiple technical security measures on the perceived usability and security are opposing, when the perceived security level increases by implementing a technical security measure, the perceived usability level decreases and the other way around. This research also reveals that in general employees consider usability and security as equally important in their choices for technical security measures.