Abstract--Traditional cybersecurity tabletop exercises (TTXs) provide valuable training but are often scripted, resource-intensive, and difficult to scale. We introduce AgentBnB, a browser-based re-imagining of the Backdoors & Breaches game that integrates large language model teammates with a Bloom-aligned, retrieval-augmented copilot (C2D2). The system expands a curated corpus into factual, conceptual, procedural, and metacognitive snippets, delivering on-demand, cognitively targeted hints. Prompt-engineered agents employ a scaffolding ladder that gradually fades as learner confidence grows. In a solo-player pilot with four graduate students, participants reported greater intention to use the agent-based version compared to the physical card deck and viewed it as more scalable, though a ceiling effect emerged on a simple knowledge quiz. Despite limitations of small sample size, single-player focus, and narrow corpus, these early findings suggest that large language model augmented TTXs can provide lightweight, repeatable practice without the logistical burden of traditional exercises. Planned extensions include multi-player modes, telemetry-driven coaching, and comparative studies with larger cohorts. Cybersecurity tabletop exercises (TTXs) [1]-[3] have long served as a core method of incident-response training, giving teams structured environments to practice technical and organizational decision-making under pressure.

With the aim to provide teachers with more specific, frequent, and actionable feedback about their teaching, we explore how Large Language Models (LLMs) can be used to estimate ``Instructional Support'' domain scores of the CLassroom Assessment Scoring System (CLASS), a widely used observation protocol. We design a machine learning architecture that uses either zero-shot prompting of Meta's Llama2, and/or a classic Bag of Words (BoW) model, to classify individual utterances of teachers' speech (transcribed automatically using OpenAI's Whisper) for the presence of Instructional Support. Then, these utterance-level judgments are aggregated over an entire 15-min observation session to estimate a global CLASS score. Experiments on two CLASS-coded datasets of toddler and pre-kindergarten classrooms indicate that (1) automatic CLASS Instructional Support estimation accuracy using the proposed method (Pearson $R$ up to $0.47$) approaches human inter-rater reliability (up to $R=0.55$); (2) LLMs yield slightly greater accuracy than BoW for this task, though the best models often combined features extracted from both LLM and BoW; and (3) for classifying individual utterances, there is still room for improvement of automated methods compared to human-level judgments. Finally, (4) we illustrate how the model's outputs can be visualized at the utterance level to provide teachers with explainable feedback on which utterances were most positively or negatively correlated with specific CLASS dimensions.