Many island endemics are of great conservation concern due to small range and population sizes. The Montserrat Oriole Icterus oberi is a forest passerine endemic to the Caribbean island of Montserrat, where recent volcanic activity has destroyed a large proportion of suitable forest habitat. From 1997 to 2000 the Montserrat Oriole population declined dramatically even in the remaining forest habitat, leading to its classification as ‘Critically Endangered’. We present trend estimates of the Montserrat Oriole population from 2000 to 2013, and estimate the world population size in 2012 based on repeat point counts and beta-binomial mixture models. Montserrat Orioles recovered between 2003 and 2005, and we found no evidence for a continuing population decline. However, there was large uncertainty around trend estimates, and the power to detect a shallow negative trend was very low. Based on the comparison of count data at 42 points, the Montserrat Oriole population in 2013 was less than half as large as in 1998. To improve future trend estimates a new monitoring design was introduced in 2011, and applied to all subpopulations of the species in 2012. The world population in 2012 was estimated to hold between 307 (95% credible interval 212–503) and 690 birds (476–1131) birds in the two forest fragments on Montserrat, depending on whether the sampling area around each point count was assumed to encompass 100 m or 150 m. Based on these estimates, the Montserrat Oriole currently does not meet the IUCN criteria for ‘Critically Endangered’, and we recommend a revision of the species’ conservation status.