This article reports results from a study in which two groups of college level students were exposed to interactions with Apple's Siri in order to foster dialogue about their dialectal features. In this paper, the methodology and procedural challenges behind one of the activities that the participants completed are studied. These activities had been designed to present to them the historical dimensions of the Historical California Spanish dialect, or Californio Spanish, and pursue two different outcomes for the participants: 1) to foster the interest in discovering a dialectal past, and 2) to increase linguistic self-esteem, as a result of an external validation provided by technology.