Monitoring parrot populations is of high importance because there is a general lack of quantified population trends for one of the most threatened avian orders. We surveyed parrots in Nicaragua in 1995, 1999, 2004, and 2013 at a minimum of 227 points within 56 sites stratified among the Pacific, Central Highlands, and Caribbean biogeographical regions to assess population trends. From point-count data we calculated encounter rate, flock rate, and flock size metrics and we used presence/absence data to generate species-specific occupancy estimates. Encounter rate, flock rate, and flock size data suggested family-level declines from 1995 to 2004 with some recovery between 2004 and 2013. Patterns of parrot occupancy varied among species with four decreasing, five increasing, and two with no detectable change. Six species of conservation concern are identified, including the Critically Endangered Great Green Macaw and Yellow-naped Parrot, additionally Olive-throated Parakeet, Scarlet Macaw, Brown-hooded Parrot, and White-crowned Parrot, only listed as Least Concern. All six are likely suffering from deforestation and potential unchecked trade activity in the Caribbean. Differing population trends of the regionally disjunct Yellow-naped Parrot subspecies suggest a link to variable deforestation and trade pressure experienced between the Pacific and Caribbean. Our results highlight the importance of actively monitoring changing parrot populations, even when considered Least Concern, so that directed conservation actions can be taken if needed.