Recently, the court of Milan has seized 779 million euros from Airbnb, the largest web service in the short-term homestay market. According to investigation, the digital goliath failed to pay its taxes for the Italian market in the years 2017 to 2021. Many things have changed since Airbnb was celebrated as the magic pill for putting renters directly in touch with travelers, benefitting both. Nowadays, the Californian company is losing control of its own narrative, as it finds itself at the center of controversy, fines, and tax issues as well as being accused of transforming neighborhoods and emptying city centers. A new wind is blowing, and the app giants are finding it harder to continue playing the part of the “good guys”.