(1) Background: One possible way to investigate the potential impact or susceptibility of buckling on different manual techniques is to measure compressive loads during canal negotiation. The higher their values, the easier and quicker the critical load level to buckling is reached, leading to possible instrument lateral deformation. The objective of the present study was to investigate the impacts of compressive loads on a small K-file manipulated with different techniques for canal negotiation in simulated narrow and curved canals. (2) Methods: The tooth model selected was a plastic double-curved premolar 23 mm long (DRSK Group AB, Kasernvagen 2, SE-281 35, Hassleholm, Sweden) with an extremely narrow canal lumen to mimic a very difficult anatomical scenario. An experienced endodontist performed the negotiation of 90 of these artificial teeth randomly assigned to 3 different groups of 30 blocks each, respectively, using 3 different techniques: Group A: watch winding/pull (WW) motion; Group B: balanced forces (BF) technique; Group C: envelope of motion (EOM). The measurement system was based on the use of a dynamometer, Instron, Ltd. (model 2525-818 2kN f.s.), linked to a data acquisition unit HBM MGC+ to test all the compression and tensile loads, including all the peaks. (3) Results: All data acquired were processed by the CATMAN AP HBM software. Multiple comparisons for the highest compressive loads estimated the mean difference between WW vs. BF techniques of 3.60 [95% confidence interval (CI): 2.85 to 4.35, p < 0.001], WW vs. EOM of −1.76 (95% CI: −2.11 to 1.40, p < 0.001), and BF vs. EOM −5.36 (95% CI: −6.04 to −4.67, p < 0.001). (4) Conclusions: In conclusion, among the tested manual motions, the BF technique (Group B) was the most susceptible to buckling with the highest compressive load. WW motion (Group A) and EOM (Group C) were less susceptible to buckling than the BF technique. Therefore, a pressure-free manipulation of manual files, such as WW motion or EOM, can help reduce the susceptibility to buckling during the negotiation of narrow-curved canals.