This chapter explores the meaning and relevance of the traditional policyholder’s duty of disclosure under the assumption that the historical information asymmetry between an insurer and a prospective policyholder has reversed in cases where insurers assess the risk with the use of new technology (such as tracking devices). In some instances, advanced techniques of risk monitoring allow insurers to know and manage the risk better than the actual risk bearer. Where this is the case, doubts may arise whether it still makes sense for the policyholder to disclose information on the risk. To see if there are grounds to claim that the duty to disclose loses its relevance as the insurers’ knowledge about the risk advances, the chapter analyses whether the available technology may replace this legal construct altogether. The analysis concludes that while the advanced technology may reverse the information asymmetry and therefore insurers would not need to rely on the policyholder’s knowledge about the risk, there are limits and concerns which make the thesis on the obsolescence of the duty of disclosure unwarranted.