In April and May 1644, an armed confrontation broke out in Macau between part of the city’s Christian community – largely composed of Asian-born and mixed-descent Portuguese – and the royal-appointed governor and captain-general. The details of these events are scarce, and their precise causes remain uncertain. In his later defense, the governor, Sebastião Lobo da Silveira, would claim that the rebels – whose leaders were those involved in trade with Manila – sought to restore Macau’s allegiance to the Hispanic Monarchy, thus opposing the city’s widespread acclamation of King João IV in June 1642, when news of the Portuguese Restoration first arrived. While this claim is not implausible, it cannot be confirmed given the current state of knowledge. These acts of insurgency may also have been linked to struggles between competing powers and factions within the city, or they may have represented a sudden eruption of the latent tensions always opposing the local community to royal authority. The fact is that three years later, in 1647, in another event with unclear contours, a new governor, Diogo Coutinho Docem, would be confronted with renewed armed unrest among Macau’s citizens, ultimately leading to his assassination. What makes these events particularly noteworthy is their violence, which fell outside the logic of negotiation and compromise that typically resolved the recurring conflicts that shaped Macau’s entire history. At their root may have been the intense economic, political, and social strain experienced by Macanese society amid the adverse context of the 1640s: civil wars in China during the Ming–Qing transition, pressure from the Dutch, the end of trade with Japan, the Portuguese Restoration, and the likely severing of ties with Spanish domains in Asia.