This chapter investigates situations where different players possess different levels of information, leading to strategic behaviour like brinkmanship, bluffing, and signalling. Beginning with the theory of hardball tactics, it analyses how information asymmetry influences high-stakes geopolitical games—such as US–North Korea relations, Indo-Pakistani conflicts, and the war in Ukraine. The concept of pseudo-brinkmanship is introduced to describe a situation in which one of the players secretly prefers the situation of mutual destruction to compromise. The second half of the chapter explores signalling games, including the well-known Beer–Quiche game, and applies them to political, bureaucratic, and educational settings. The chapter demonstrates that strategic communication under uncertainty is both pervasive and perilous, requiring nuanced understanding of belief systems and credibility.