A brief, confident promise of automated assistance was enough to shatter travel dreams when immigration reality got in the way—leaving a couple stranded at the airport and exposing the risks of taking digital shortcuts without verification.
Spain, August 2025. Mery Caldass and her partner, known for sharing adventures and travel tips on social media, placed full trust in ChatGPT to plan their farewell trip to Puerto Rico. When they asked if a visa was required to enter the island, the chatbot replied that no special authorization was needed. Confident in the answer’s accuracy, they headed to the airport without giving it another thought.
The reality hit hard: although Puerto Rico does not require a visa for Spanish citizens, it does require prior electronic authorization (ESTA). Without it, they were denied boarding and missed their flight. Mery’s tears, captured in a viral TikTok video, revealed not just personal frustration but also a blow to the credibility of a tool often perceived as highly competent.
ChatGPT respondió mal a pregunta de jóvenes españoles que iban a viajar al caribe y terminaron perdieron el vuelo. (Foto: TikTok)
From that moment, important questions emerged: how wise is it to delegate critical decisions to a digital assistant without consulting an official source? Experts in international mobility warn that artificial intelligence tools—despite their natural language fluency—can create a false sense of certainty, especially when it comes to legal or immigration matters. Mistakes like this are not unique to chatbots: search engines, blogs, and forums can also contain outdated information. The difference is that a chatbot, with its confident and accessible tone, can persuade without offering official backing.
This incident mirrors other cases in which AI-generated recommendations led to non-trivial consequences—from medical errors to financial losses. Contrary to popular belief, even the most advanced digital tools should serve only as a starting point, never as the ultimate authority. In this case, a single omission—the failure to mention the ESTA requirement—was enough to turn a dream trip into a bitter experience, albeit one filled with viral reach. Mery, with humor amid tears, joked that the mistake might have been “revenge” from the AI after she had previously insulted it for earlier errors.
ChatGPT respondió mal a pregunta de jóvenes españoles que iban a viajar al caribe y terminaron perdieron el vuelo. (Foto: TikTok)
Eventually, the couple made it to Puerto Rico and attended the Bad Bunny concert they had planned for. But what remains is a clear warning: enthusiasm for artificial intelligence should never overshadow caution. Checking migration regulations on official government portals is essential—especially when travel involves shared political and regulatory frameworks, as is the case with U.S. territories.
This piece was developed by the Phoenix24 editorial team using reliable sources, public data, and rigorous analysis in alignment with the current global context.