The sense of uncertainty and fragility due to the effects and magnitude of global challenges we are facing (from pandemic circumstances to climate change impacts) requires – much more than in the past – the capacity to generate a visionary and forefront design approach in the young gen-erations aiming at stimulating their reaction attitude rather than providing consolidated tools from past conditions that no longer exist or will rapidly evolve. Within this general framework, we have investigated the effectiveness and impacts of experienced-based methods of learning and innovative educational tools in architecture aimed at shaping expertise in which the environ-mental dimension and the climate-change challenge dialogues with the context's complexity in terms of socio-cultural dynamics, real potentialities and constrains, addressing their transdisci-plinary trajectories. The paper analyses 5 international pioneering teaching experiences that provide the opportunity to understand the outcomes of collaborative and experiential learning processes in which the educational activities leverage a dialogue between diverse communities (academia-citizens-policymakers-practitioners). The study outcomes show that shifting the pedagogical paradigm towards in-field-experience-based models can improve the awareness of future practitioners for climate implications of architectural design, implement their analysis and project skills while triggering processes of knowledge transfer and co-production at community level, and allow them to better address the societal and cultural issues involved within decision making.