Considering the uncertainty of upper-stem diameter measurements and the fact that there are few studies on the accuracy of diameters using the Mantax Black caliper with Gator Eyes (Haglöf, Långsele, Sweden), the aim of this research is to check laser caliper reliability in upper-stem diameter measurements. The study was conducted in Parc Aventura Braşov (Romania), where a target tree was marked with visible signs at 1 m, 3 m, 5 m, 7 m, 9 m, and 13 m above the ground, and the diameters of the six sections were measured using a conventional caliper and climbing equipment. Later on, 14 forest mensurationists used a laser caliper to measure the diameters of the marked sections 13 m away from the tree, maintaining the direction of measurement. Each user performed repeated independent measurements of the upper-stem diameters, resulting in 14 data sets with 10 values for every section and a total number of 840 observations. Applying ANOVA for all the sections, we found that there are significant differences between the data sets collected by many users, and the pairwise t-test and the Benjamini-Hochberg method showed significant differences. Taking into account the analysis of the individual errors in measuring the upper-stem diameters using a laser caliper, we were able to identify the data sets affected by abnormal errors. By measuring the diameters along the stem up to 13 m above the ground using a laser caliper, one out of 2.4 measurements up to one out of approximately 1.5 was determined with an error below 2 cm. At heights above 5 m, a maximum of one out of five measurements was affected by errors above 4 cm. In addition, it was noted that there is generally a tendency to underestimate the upper-stem diameter and volume estimate when the laser caliper is used for the measurements. The absolute mean error varied between 1.46 cm and 2.52 cm along the stem and the root mean squared error varied between 1.84 cm and 3.04 cm. Nevertheless, general uncertainty about this subject remains, because if we measure upper-stem diameters without contact with the trunk, we will never know whether a single reading shows a negligible error to be used for calibrating taper equations or for increasing volume estimation accuracy. Consequently, we recommend that when used for this purpose, diameters should be measured several times, by experienced users who have proven their skill in measurements that yield smaller errors.