Virtual Teaching Assistants (VTAs) can reduce the workload of teaching teams in Asynchronous Learning Environments (ALEs) where timely, personalized support is often limited. As VTA systems grow more capable, rigorous and pedagogically sound evaluation becomes essential. Existing assessments often rely on surface-level metrics and lack sufficient grounding in educational theory, making it difficult to meaningfully compare the pedagogical effectiveness of VTA systems. To bridge this gap, we propose a pedagogically-oriented evaluation framework that is rooted in learning sciences and tailored to asynchronous forum discussions, a common VTA deployment context in ALE. We construct classifiers using expert annotations of VTA responses on a diverse set of forum posts. We evaluate the effectiveness of our classifiers, identifying approaches that improve accuracy as well as challenges that hinder generalization. Our work establishes a foundation for theory-driven evaluation of VTA systems, paving the way for more pedagogically effective AI in education.

Existing English-teaching chatbots rarely incorporate empathy explicitly in their feedback, but empathetic feedback could help keep students engaged and reduce learner anxiety. Toward this end, we propose the task of negative emotion detection via audio, for recognizing empathetic feedback opportunities in language learning. We then build the first spoken English-teaching chatbot with adaptive, empathetic feedback. This feedback is synthesized through automatic prompt optimization of ChatGPT and is evaluated with English learners. We demonstrate the effectiveness of our system through a preliminary user study.

Dialogue systems have been used as conversation partners in English learning, but few have studied whether these systems improve learning outcomes. Student passion and perseverance, or grit, has been associated with language learning success. Recent work establishes that as students perceive their English teachers to be more supportive, their grit improves. Hypothesizing that the same pattern applies to English-teaching chatbots, we create EDEN, a robust open-domain chatbot for spoken conversation practice that provides empathetic feedback. To construct EDEN, we first train a specialized spoken utterance grammar correction model and a high-quality social chit-chat conversation model. We then conduct a preliminary user study with a variety of strategies for empathetic feedback. Our experiment suggests that using adaptive empathetic feedback leads to higher *perceived affective support*. Furthermore, elements of perceived affective support positively correlate with student grit.