This research explores the awareness and adoption of one-trip insurance among different generational groups, namely Gen X, Gen Z, and Millennials. Utilizing a qualitative research design with purposive sampling and interview method of data collection, the study involved 24 participants, with eight individuals representing each generation. The findings of this study conclude that in-trip insurance is not a popular choice of security among most of the sample due to lack of awareness about the specific policy and insurance in general. Other barriers include cost, distrust in the system and utility of the insurance and false optimism.