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The objective of this study is to evaluate the retreatment time and weight of apically extruded debris yielded by two different kinematics during the removal of different root canal filling materials. Forty straight single-rooted extracted teeth were instrumented with HyFlex CM files and obturated with two different techniques: 25.04 HyFlex experimental carrier-based obturators (Coltène/Whaledent, Altstätten, Switzerland) (group 1) or 25.04 single gutta-percha cones (Roeko Coltène/Whaledent, Altstätten, Switzerland) (group 2) and Guttaflow Bioseal as the sealer. Samples were divided into four subgroups (n = 10) according to the used kinematics for the removal of root canal filling materials: continuous rotation (A) or retreatment motion (B) with a Remover and HyFlex EDM Nickel-Titanium instruments activated with a CanalPro Jeni micromotor (Coltène/Whaledent, Altstätten, Switzerland). Time for retreatment was digitally recorded, and debris extruded from the apex was collected in Eppendorf tubes and weighted with an analytical balance. Data on retreatment time and apical extrusion were statistically analyzed with the Kruskal–Wallis test (p < 0.05). Working length was achieved in all the retreated samples. The removal of root filling material resulted significantly faster with the Jeni mode (p < 0.001), and the difference was significant for the removal of both filling materials (p < 0.05). No significant differences on debris extrusion between single cone and experimental obturators groups were noted (p > 0.05), and no significant differences between kinematics (continuous rotation vs. Jeni motion) were observed (p > 0.05). All the tested retreatment strategies lead to an extrusion of material from the apex, and the weight of apically extruded debris was similar. The use of the innovative CanalPro Jeni kinematics accelerates the time for the removal of root filling materials. [ABSTRACT FROM AUTHOR]