The current panorama of AI-infused devices portrays a significant dominance of first-party smart speakers, which appear to be the first massive embodiment of AI in the domestic landscape. These devices are nothing more than discreet ornaments, looking at their simple phys- ical appearance. Although, the simple appearance betrays a complexity determined by numerous features that make such products challenging to analyze from a UX point of view. The main evident characteristic is that they are not just “simple products” but ecosystems consisting of several interfaces and touch- points. Most of them integrate multiple interfaces – namely physical, digital, conversational – sometimes overlapping. The second element of complexity resides in their technological core, based on learning algorithms. Therefore, the same device can provide different outputs at the same input over time, a condition that can affect the user experience. To increase the complexity of these devices, at least from a UX standpoint, there is the fact that their real potential is rarely exploited by most users, which mainly uses routine actions such as reading news, weather forecasting, and controlling simple home appliances. Accordingly, the chapter frames the wicked relationship between user experience and AI-infused products. Moving from the three iden- tified elements of the complexity of AI-infused products, it advances reflection on how it could be possible to analyze these products from a UX standpoint.