Wearable devices increasingly support stress detection, while LLMs enable conversational mental health support. However, designing systems that meaningfully connect wearable-triggered stress events with generative dialogue remains underexplored, particularly from a design perspective. We present EmBot, a functional mobile application that combines wearable-triggered stress detection with LLM-based conversational support for daily stress management. We used EmBot as a design probe in semi-structured interviews with 15 mental health experts to examine their perspectives and surface early design tensions and considerations that arise from wearable-triggered conversational support, informing the future design of such systems for daily stress management and mental health support.

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