Landscape architecture’s digital transformation is increasingly tied to collaborative, datarich processes that blend community insights with computational modeling. We propose the integration of Kairos Moments, pivotal opportunities for timely reflection and action, into a digital twin-supported participatory design framework. In a one-year community design project in a mid-sized city in upstate New York, spatial data on heat, flood risk, walkability, and demographics were embedded in a webbased digital twin to facilitate stakeholder deliberation and iterative scenario development. The framework uses heuristic cues (based on Tversky & Kahneman’s cognitive biases) to classify engagement episodes as representativeness, availability, or anchoring adjustments, which in turn flag Kairos Moments when collective decisions are most opportune. These moments serve as a bridge between realworld events and the digital twin environment, synchronizing community momentum with design interventions. Results indicate that the interactive digital twin improved transparency and allowed participants to visualize trade-offs, while the Kairos-based timing analytics enhanced stakeholder trust and foresight by aligning design actions with critical community readiness. We conclude with practical recommendations for embedding Kairos-informed, ethically grounded digital methods in participatory design practice and institutional policy.