This is a prototype role-playing simulation where the user tutors a library patron through a technology learning or troubleshooting session. The goal is to provide training for Socratic Tutoring techniques and a way to learn how to work one-on-one with students. The scenario focuses on a specific patron, Cindy, with defined background, skills, goals, and challenges related to email, requiring the user to employ effective Socratic Tutoring techniques to help her achieve her objectives and resolve her immediate question, while also accounting for potential real-world complications with her device. The simulation ends when the user has successfully guided Cindy to a point where she feels confident in her ability to send emails with attachments, organize her inbox, and understand basic email safety related to her initial question and goals. Once the simulation concludes, the user receives advice focusing on the effectiveness of their teaching approach and areas for potential growth. It is important to note that this demonstration application does not record any personal information, nor does it utilize any information entered to train our artificial intelligence systems. Conversation history is erased upon refreshing the page.