Population aging resulting from demographic changes requires some challenging decisions and necessary steps to be taken by different stakeholders to manage current and future demand for assistance and support. The consequences of population aging can be mitigated to some extent by assisting technologies that can support the autonomous living of older individuals and persons in need of care in their private environments as long as possible. A variety of technical solutions are already available on the market, but privacy protection is a serious, often neglected, issue when using such (assisting) technology. Thus, privacy needs to be thoroughly taken under consideration in this context. In a three-year project PAAL (‘Privacy-Aware and Acceptable Lifelogging Services for Older and Frail People’), researchers from different disciplines, such as law, rehabilitation, human-computer interaction, and computer science, investigated the phenomenon of privacy when using assistive lifelogging technologies. In concrete terms, the concept of Privacy by Design was realized using two exemplary lifelogging applications in private and professional environments. A user-centered empirical approach was applied to the lifelogging technologies, investigating the perceptions and attitudes of (older) users with different health-related and biographical profiles. The knowledge gained through the interdisciplinary collaboration can improve the implementation and optimization of assistive applications. In this paper, partners of the PAAL project present insights gained from their cross-national, interdisciplinary work regarding privacy-aware and acceptable lifelogging technologies.