Mathematical Argumentation skills have historically been overlooked in assessment, but the inclusion of Mathematical Argumentation in the Common Core State Standards (CCSS) as one of the Standards of Mathematical Practice challenges assessment developers to assess this mathematical practice. Explanation and justification of one's own thinking to a specific audience is considered a fundamental part of this mathematical practice. Based on student demonstration of argumentation skills when engaging with peers, we have developed automated conversations with virtual teachers and peers to investigate how alternative conversational patterns influence types of student responses. This technology allows assessment developers an innovative avenue for exploring new task designs that adapt to individual users and produce additional data not found in traditional measures. Preliminary findings from this investigation are presented. [For the complete proceedings, see ED583608.]