Purpose/objectivesThis prospective crossover preclinical trial aimed to evaluate the learning curve of dental students in successfully administering intraligamentary anesthesia (ILA) using three different syringe systems.MethodsDental students performed ILA using three devices in two separate sessions, each targeting mandibular and/or maxillary premolars. The devices included two manual systems (pistol‐type and lever‐based) and one computer‐controlled local anesthetic delivery system (CCLAD). The primary research parameter was the success rate of anesthesia, defined as the percentage of successful ILA administrations confirmed by a negative response to a cold test. Secondary parameters included pain experienced during needle penetration and injection, students' self‐reported levels of mental tension and handling of the syringes, and any potential side effects.ResultsA total of 110 students performed ILA on 599 teeth during the study period. When comparing the CCLAD system to the manual syringes, the CCLAD system exhibited a significantly higher overall success rate in the first session (92.5% vs. 77.4%; p < 0.001), potentially due to its precise control of anesthetic flow and pressure, which likely facilitated more effective anesthetic delivery. However, when examining the individual manual techniques, no significant difference was found between the pistol‐type manual and the CCLAD system (p = 0.66). All techniques' success rate increased from the first to the second session (80.4% vs. 86.9%; p = 0.0357). Additionally, penetration pain demonstrated a significant decrease across all techniques (p < 0.01). Notably, students' anxiety levels decreased, and self‐assurance increased significantly over the sessions. Undesired reversible side effects were documented in 10.9% of cases.ConclusionThese findings suggest that repeated practice of ILA, particularly with different syringe systems, enhances anesthetic success and psychological readiness for patient interaction. Additional training sessions may further improve proficiency.