Elon Musk has gone down quite the rabbit hole when it comes to tech and robots. While this often offers incredible potential, it can, at times, be risky. The billionaire entrepreneur came to international attention when he promised a revolutionary anti-woke chatbot that would challenge people engaged in damaging conversations online. His vision was for the bot to engage in online conversations, then provoke discourse by making comments that challenged traditional notions of identity or political correctness. However, it seems that the chatbot has not been received that warmly by the public. Critique has focused on both the lack of success in challenging dangerous conversations and the potential risks of attempting to promote the anti-woke agenda. One of the main problems with the idea is that it is effectively a battle of wits between automated chatbots whom simply cannot have debates in the same way as a human. To the AI avatar, issues such as race and gender cannot be discussed as eloquently or deftly as a person could, meaning the anti-woke agenda has limited effectiveness. The second issue is that such an anti-woke agenda could expose people to dangerous conversations that can be damaging. As anyone who’s ever had an online spat can attest, the language used in online debates are often crude and confrontational, and this can lead to a level of harm and danger that is not conducive to positive conversation, no matter the subject. Ultimately, Musk’s attempt to bring an anti-woke bot to the web to act as a challenge to dangerous conversations, was noble and worthy of recognition. However, he must now consider that the risks to individuals engaging in these conversations, and the efficacy of such a bot, both warrant further re-evaluation and consideration.