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Military alliances are an essential cornerstone of the international system. However, scholarship often overlooks how states strategically manage the alliance design process to address their core concerns regarding abandonment and entrapment. This dissertation argues that the states manipulate the level of precision regarding activation conditions and the degree of institutionalization of military integration, which combine to define the depth of the alliance agreement to mitigate the risks of abandonment and entrapment. In Chapter 1, using a large-n analysis of bilateral defensive military alliances post-WWII, I assess how state reliability influences alliance design. My results indicate the presence of a non-linear relationship: institutionalization initially decreases as weak state reliability increases before increasing. In contrast, precision increases as strong state reliability increases before tapering off. In contrast to expectations, deeper alliances correlated with a higher likelihood of conflict, suggesting states may form alliances in anticipation of conflict or that deeper agreements embolden more risky behavior by allies. In Chapter 2, I employ a survey experiment of UGA students to evaluate how variation in threat level and alliance precision influence the perception of reputational damage from violating an alliance and alliance commitment. My results indicate that precise agreement increases the expected reputational damage and the feelings of alliance commitment. However, if weaker alliance partners seek to renegotiate the terms of the alliance agreement, feelings of alliance commitment abate. In Chapter 3, I survey South Korean citizens to assess how variation in alliance partner reliability impacts respondent attitudes regarding alliance security and renegotiation efforts. I find that unreliable partners reduce trust in the agreement and increase South Korean citizens’ desire to lessen the degree of military integration between allies. Together, these studies demonstrate how variation in state reliability influences how prospective allies approach the alliance negotiation process, leveraging the dimensions of both precision and institutionalization to address their key concerns.