There are a range of popular tree hypsometer or height finding devices in popular use in the New Zealand forestry sector, but they have not been rigorously testing in New Zealand plantation forestry conditions against independently measured tree height via direct measurement after felling. Using instruments provided by the University of Canterbury’s School of Forestry that represent the diversity of contemporary hypsometers used in New Zealand forestry, the research explored the bias and precision via parametric and non-parametric statistical testing as appropriate of said instruments in ideal measuring conditions, as well as in actual radiata pine (Pinus radiata D.Don) plantations in the Christchurch area. The study instruments were evaluated on 100 radiata pine stems located across three different sites, and multiple measurements were taken by three operators using all five instruments. In addition to the intended use by hand, the study instruments were used with a monopod to test if height measurement bias and precision were affected and time taken to measure stems was recorded for each method. Additionally, given the increasing ubiquity of drone-based LiDAR use in forestry, fair comparisons were made between its height measurement bias and precision results and those of the study instruments using the same statistical methods. In field conditions the EC II-D, Vertex 5, and Vertex Laser Geo stood out as having less bias than other instruments (p > 0.05) while not being different from each other in terms of bias and precision (p < 0.05). Drone-based LiDAR bias of tree height measurements was not significantly different from the study instruments (p < 0.05) except for the Forestry Pro II. Ultimately, which technology to use for forest management will be decided by foresters and other stakeholders based on time, budget, and level of metric fidelity dictated by management goals.