Studying interactions of children with humanoid robots in familiar spaces in natural contexts has become a key issue for social robotics. To fill this need, we conducted several Child–Robot Interaction (CRI) events with the Pepper robot in Polish and Japanese kindergartens. In this paper, we explore the role of trust and expectations towards the robot in determining the success of CRI. We present several observations from the video recordings of our CRI events and the transcripts of free-format question-answering sessions with the robot using the Wizard-of-Oz (WOZ) methodology. From these observations, we identify children’s behaviors that indicate trust (or lack thereof) towards the robot, e.g., challenging behavior of a robot or physical interactions with it. We also gather insights into children’s expectations, e.g., verifying expectations as a causal process and an agency or expectations concerning the robot’s relationships, preferences and physical and behavioral capabilities. Based on our experiences, we suggest some guidelines for designing more effective CRI scenarios. Finally, we argue for the effectiveness of in-the-wild methodologies for planning and executing qualitative CRI studies.