Abstract: This paper investigates why the Spanish of sixteenth-century Panama were unable to conquer local cimarron groups until after the 1570s. By incorporating both primary and secondary sources, the paper contends that there were several reasons likely contributing to Spanish administrative failure. First, the Spanish, until the 1570s, perceived the cimarrons as a mere nuisance and thus did not focus greater efforts on eliminating or recapturing them. Second, the Panamanian cimarrons proved highly resourceful as shown by both a variety of successful attacks on Spanish settlements and even an alliance with Sir Francis Drake. This paper is limited in several respects. The sources consulted are overwhelmingly from English scholarship as the author’s knowledge of Spanish is deficient. Another limitation is the absence of any primary source accounts from the cimarrons themselves. Finally, the paper focuses solely on the history of the Panamanian cimarrons and not those from other regions across the Americas. Considering these limitations, this paper provides a case-study analysis of the extent to which the Panamanian cimarrons caused changes in Spain’s administrative policies in Panama towards the end of the sixteenth century.