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Prior work has consistently found that people have miscomprehensions and misunderstandings about technical terms. However, that work has exclusively studied general populations, usually recruited online. This work investigates the relationship between generational cohorts and their understandings of privacy terms, specifically cohorts of elementary school children (aged 10-11), young adults (aged 18-23), and retired adults (aged 73-92), all recruited offline. We surveyed participants about their understanding of and confidence with technical terms that commonly appear in privacy policies. We then moderated a post-survey focus group with each generational cohort in which participants discussed their reactions to the actual definitions along with their experience with technical privacy terms. We found that young adults had better understandings of technical terms than the other generations, despite all generations reporting being regular Internet users. Participants across all generational cohorts discussed themes of confusion and frustration with technical terms, and older adults particularly reported a sense of being left behind. Our results reinforce the need for improvement in the presentation of information about data use practices. Our results also demonstrate the need for more focused research and attention on the youngest and oldest members of society and their use of the Internet and technology.