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Children of all ages interact with speech recognition systems but are largely unaware of how they work. Teaching K-12 students to investigate how these systems employ phonological, syntactic, semantic, and cultural knowledge to resolve ambiguities in the audio signal can provide them a window on complex AI decision-making and also help them appreciate the richness and complexity of human language. We describe a browser-based tool for exploring the Google Web Speech API and a series of experiments students can engage in to measure what the service knows about language and the types of biases it exhibits. Middle school students taking an introductory AI elective were able to use the tool to explore Google’s knowledge of homophones and its ability to exploit context to disambiguate them. Older students could potentially conduct more comprehensive investigations, which we lay out here. This approach to investigating the power and limitations of speech technology through carefully designed experiments can also be applied to other AI application areas, such as face detection, object recognition, machine translation, or question answering.