Turkmenistan, as a hapless policy-taker, permeates many conventional analyses of the Central Asian states. In this chapter, I argue, however, that the ability of the Turkmen ruling elite to renegotiate the terms of engagement with regional hegemons has a significant but often underappreciated part of the narrative about small–great power relations in Central Asia. The analysis reveals that Turkmenistan has the political will and material capability to leverage advantageous domestic and external conditions to engage in selective hedging behavior against great powers. This chapter contributes to the literature on small states’ hedging strategy by applying it to the case of Turkmenistan’s foreign policy behavior in the environment of uncertainty posed by the great powers’ competing interests and hegemonic ambitions.