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This study examined how anti-phishing courses, enhanced by wearable virtual reality and smart feedback chatbots, affect older adults’ situational interest and anti-phishing self-efficacy. A total of 127 participants aged 55 and above were randomly assigned to four groups: traditional learning, VR, chatbot, and VR-chat combined. Results showed that VR and chatbots significantly enhanced situational interest across all dimensions. Chatbots notably improved self-efficacy among low-confidence learners, as confirmed via Johnson–Neyman analysis. While VR offered immersive benefits, chatbot interaction provided greater personalization and accessibility. These findings underscore the value of combining immersive and adaptive tools to promote digital resilience and safer online behavior in aging populations, offering scalable strategies for cybersecurity education and inclusive digital learning design.