The question of loyalty in autocratic regimes has drawn a sustained scholarly interest, especially as autocratic leaders need to secure the support of their militaries to survive in office and to minimize the risk of a coup. Among the commonly employed mechanisms in this regard is the extension of extra-budgetary financial rewards, including “Military-Owned Businesses (MOBs)”. Nevertheless, under the increasingly significant threat of an uprising from below, military defection remains the key for the success of the revolution. The question then becomes: under what conditions would a military defect from an autocratic ruling alliance? This paper presents one novel answer to this question, which is: militaries are “defection-proofed” in the face of mass uprisings when they develop financial dependency on the regime. This hypothesis is tested comparatively against the cases of mass protests in China (1989), Indonesia (1998), Thailand (2006), and Iran (2009).