Microsoft created an online chatbot called 'Tay' in March 2016, intended to test the limits of artificial intelligence and machine learning on social media platforms. Less than 24 hours later, Tay went off the rails.

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Sources:

• https://web.archive.org/web/20160323194709/https://tay.ai/

https://arxiv.org/abs/1812.08989

• https://www.nytimes.com/2015/08/04/science/for-sympathetic-ear-more-chinese-turn-to-smartphone-program.html

• https://www.theverge.com/2016/3/23/11290200/tay-ai-chatbot-released-microsoft

• https://www.theverge.com/2016/3/24/11297050/tay-microsoft-chatbot-racist

• https://www.businessinsider.com/microsoft-deletes-racist-genocidal-tweets-from-ai-chatbot-tay-2016-3

• https://web.archive.org/web/20170210055324/http://fusion.net/story/284617/8chan-microsoft-chatbot-tay-racist/

• https://fortune.com/2016/03/30/microsofts-tay-return/

• https://www.cnet.com/tech/mobile/microsoft-zo-chatbot-ai-artificial-intelligence/

• https://qz.com/1340990/microsofts-politically-correct-chat-bot-is-even-worse-than-its-racist-one/