In a striking reversal that reshaped the conquest narrative of Guatemala, the Kaqchikel Maya, once formidable allies of the Spanish conquistadors, ignited a resistance that thwarted colonial ambitions for several years. Residing in the southern highlands from their capital of Iximche’, the Kaqchikels initially joined forces with Pedro de Alvarado in 1524 to subdue other Indigenous polities, including their neighbors like the K’iche’s, Tz’utujils, and Pipils. While the pact between the two sides proved successful, it disintegrated within mere months, marking the beginning of a prolonged resistance that significantly delayed Spanish conquest and colonization efforts. This thesis delves into the pivotal transition of the Kaqchikels from allies to adversaries, highlighting the strategic maneuvers that underpinned their alliance and subsequent resistance with and against the Spaniards. Furthermore, it critically examines the conduct and perceptions of warfare during this dilemma. By intertwining narratives of strategy, resistance, and ideological warfare while employing Indigenous and Spanish sources, this study contributes to the nuanced reevaluation of the conquest of Guatemala, aligning with the revisionary New Conquest History.