The goal of intelligent tutoring systems (ITS) that interact in natural language is to emulate the benefits that a well-trained human tutor provides to students, by interpreting student answers and appropriately responding in order to encourage elaboration. BRCA Gist is an ITS developed using AutoTutor Lite, a Web-based version of AutoTutor. Fuzzy-trace theory theoretically motivated the development of BRCA Gist, which engages people in tutorial dialogues to teach them about genetic breast cancer risk. We describe an empirical method to create tutorial dialogues and fine-tune the calibration of BRCA Gist’s semantic processing engine without a team of computer scientists. We created five interactive dialogues centered on pedagogic questions such as “What should someone do if she receives a positive result for genetic risk of breast cancer?” This method involved an iterative refinement process of repeated testing with different texts and successively making adjustments to the tutor’s expectations and settings in order to improve performance. The goal of this method was to enable BRCA Gist to interpret and respond to answers in a manner that best facilitated learning. We developed a method to analyze the efficacy of the tutor’s dialogues. We found that BRCA Gist’s assessment of participants’ answers was highly correlated with the quality of the answers found by trained human judges using a reliable rubric. The dialogue quality between users and BRCA Gist predicted performance on a breast cancer risk knowledge test completed after exposure to the tutor. The appropriateness of BRCA Gist’s feedback also predicted the quality of answers and breast cancer risk knowledge test scores.