“Middle powers,” variously defined, have served relevant and significant roles in the post-WWII regional and global orders, facilitated by structural conditions of “long peace” among great powers and proactive leadership by and among creative middle powers. Within the complex Asia-Pacific security order, “middle powers” such as Australia, Canada, and South Korea have had the “space” to engage the non-like minded and advance multilateralism with security guarantees from the US. However, Beijing and Washington today are eliminating this space and its associated choices for middle-power diplomacy by increasingly characterizing their rivalry as a confrontation of “existential threats” between incompatible “civilizations” and securitizing trade and technology. China and the US are each selectively ignoring or purposely eroding key aspects of a rules-based international order. This paper highlights the dilemmas of South Korea, Australia, and Canada, middle powers who have found themselves individually and collectively “stuck” facing contradictory global and regional policy choices.