As more and more objects and devices get “smart” and heavily interconnected via the Internet of Things (IoT), the need for intelligent, omnipresent and individualized assistance increases rapidly. In order to develop helpful and economically viable ubiquitous intelligent assistance, companies need insights about the users’ preferences and willingness to pay for different features of Ubiquitous Intelligent Assistants (UPAs). To date, the existing body of literature does not deliver expedient information on this topic. Our study contributes to the existing research by assessing the users’ preferences and willingness to pay for a highly secure and privacy stringent UPA. Based on a Choice-Based Conjoint analysis method, we found that the participants have serious concerns about the security and privacy of their personal data. Furthermore, we discovered that participants acknowledge that for additional security and privacy a higher cost is due. However, there is a discrepancy between the user’s valuation of high security and privacy features and the actual costs incurring to realize that high level of data protection. The resulting financing gap needs to be addressed through savvy business models, which according to our findings can include advertising or product differentiation, but by no means the monetization of the participants’ personal data.