Tropical dry forests are highly threatened at a global scale. Long-term monitoring of remaining stands is needed to assess forest health, efficacy of management practices, and potential impacts of climate change. Using a multi-seasonal Landsat time series, we examined Normalized Difference Vegetation Index (NDVI) patterns in native dry forest, non-native vegetation types, and dry forest restoration sites from 1999 to 2022 in the Hawaiian Islands. We calculated trends in median NDVI and robust coefficient of variation of NDVI for dry and wet seasons, and used Breaks for Additive Seasonal and Trend analysis to detect trend departures. To assess the impact of regional drying trends, NDVI trends were compared to the seasonal long-term precipitation anomaly and cumulative precipitation anomaly. We found that native dry forest was less green than non-native forest, particularly during the dry season, and that median NDVI increased in both native and non-native dry forests over the study period despite negative precipitation anomaly trends. This result differs from coarser-scale studies in Hawaii, but is supported by trends in other dry forest regions. Greening was also observed in restoration study sites, especially larger sites where native species establishment and recruitment has been reported. Non-native grassland NDVI exhibited a strong positive link to precipitation anomalies, suggesting that drier climate scenarios may exacerbate the invasive grass-wildfire cycle that threatens native dry forest. These results demonstrate that Landsat time series may be used to detect seasonal variation in dry forest plots and to support restoration site monitoring in a highly fragmented ecosystem.