Tropical montane forests are being lost at an alarming rate but harbor some of the globe’s most unique biodiversity. The Hawaiian archipelago is a prime example of the importance of high elevation forests to species conservation and persistence as they serve as the last refugia for Hawaiian birds. Yet these forests have been converted to invasive dominated pastures, and efforts to restore them have been met with limited success. Unsuccessful forest restoration may be due to freezing temperatures acting as a demographic bottleneck by killing seedlings recruiting into pastures. We determined freezing tolerances of eight common native woody plants at a high-elevation forest on Hawaiʻi Island and compared these freezing tolerances to two years of site-specific winter temperatures and 17 years of regional temperature records. Low temperature extremes were more severe and common in pastures than under nearby 30-year-old canopy trees. Freezing temperatures over two years were severe enough to damage leaf tissues of six of eight species tested. Those species that displayed the greatest freezing tolerance were also those found naturally recruiting into open pastures. Temperature trends over the past 17 years show monthly minimum temperatures are not increasing as predicted by climate change. Persistent severe freezing events may limit seedling recruitment in the pasture, slowing native woody plant expansion into these abandoned pastures. The species-level differences in freezing tolerance show that current management actions are using species that are at high risk to freezing damage outside of the forest canopy and that alternative species may warrant consideration.