AI generational challenges in Bulgaria, as worldwide, revolve around the different ways in which older and younger generations interact with and adapt to emerging technologies like artificial intelligence (AI). These challenges arise due to variations in digital literacy, workforce readiness, educational systems, and even cultural attitudes toward technology. Younger Bulgarians, particularly those in urban areas, tend to be more familiar and comfortable with AI and digital technologies. They grow up in a tech-savvy world, receive digital education, and are exposed to AI-based tools and services in their daily lives. Older Bulgarians may struggle to adapt to these technologies due to lower digital literacy and a more traditional approach to work and life. Many older individuals may find it challenging to transition to AI-based tools and automation, leading to a gap in understanding and usage between generations. Pre-school children and ageing people are most vulnerable AI users. This study aims to trace trends in the attitudes of the Bulgarian generations to the AI challenges. The methodology includes comparative analysis of statistical data, policies, and the results of a conducted empirical survey.