Amazon's struggle to update Alexa with generative AI technology has highlighted the challenges companies face in revamping digital assistants built on older technologies. The company was caught off guard by the launch of OpenAI's ChatGPT and lacked the necessary expertise and resources to build massive language models. Despite demonstrating a new generative AI-powered Alexa, the feature has yet to be released due to technical and bureaucratic problems. Former employees say the project was plagued by dysfunction, inadequate resources, and a lack of vision, making it difficult for Alexa to transition from taking commands to enabling conversational dialogue.