We explore why AI isn’t bridging the gap between polished prototypes and working code, but rather exposing how little we understand about the handoff. Christine Vallaure maps the semantic failures in Figma-to-code pipelines, while Victor Yocco argues that forcing chat interfaces on high-cognitive-load tasks fails the user. We also weigh the human cost of walled gardens against the digital fatigue of complex productivity tools, asking what happens when the map no longer matches the territory.