A recent YouGov survey commissioned by Mashable found that the majority of U.S. adults have used an artificial intelligence chatbot like Claude or ChatGPT. To understand the details of such use, Mashable interviewed three different people: a grandmother, an entrepreneur, and a technologist. Last fall, Barbara, 71, teamed up with her son and daughter-in-law to use ChatGPT to help understand whether her grandson, who has a learning disability, was achieving the learning goals set by his school district. If the district answered affirmatively, they could argue her grandson no longer needed classroom support. The family turned to the chatbot for clarity amidst a brewing confrontation with school staff. Barbara, a former educator, felt overwhelmed by the documentation her grandson had accumulated over years of elementary school, including grades, test scores, and cognitive and intellectual ability tests. They uploaded all the paperwork, and via direct prompting, the model also considered the state's education disability law and regulations, as well as an uploaded copy of the Department of Education's Individuals with Disabilities Education Act handbook. ChatGPT ultimately sided with Barbara and her family. Barbara said the chatbot did not return a single smoking-gun finding or ironclad strategy.