Information security awareness (ISA) programs play an important role in enhancing employees’ information security knowledge and information security behavior. A variety of delivery methods, such as training, workshops, posters, have been employed in ISA programs. Recently, AI chatbots have appeared as interactive and adaptive educational tools to enhance users’ learning experiences, implying their potential use within ISA programs. This study aims to examine potential challenges with the use of AI chatbots within ISA programs from information security managers’ perspectives. To address this, a qualitative study through semi-structured interviews with eight information security managers was carried out in Sweden. The collected data were analyzed using thematic analysis. The analysis yielded three identified main themes: adoption challenges, deployment challenges, and ethical challenges. The deployment challenges were further divided into two sub themes: organizational and technical. This research contributes to the current literature on the use of AI chatbots within ISA programs. Furthermore, the findings also offer valuable insights for information security managers to understand what factors should be considered when integrating AI chatbots into their current ISA programs.