Microsurgery is a technically demanding surgical discipline with a steep learning curve. Trainees have faced several difficulties due to less hands-on theater time and pandemic-related limits on access to technical training. To overcome this, trainees engaged in self-directed training, which requires an accurate self-assessment of skill. This study aimed to assess the ability of trainees to accurately self-assess their performance while performing a simulated microvascular anastomosis. Novice and specialist plastic surgery trainees performed a simulated microvascular anastomosis on a high-fidelity chicken femoral vessel model. Each participant objectively rated the quality of their anastomosis using the Anastomosis Lapse Index (ALI). Two expert microsurgeons subsequently blindly rated each anastomosis. To determine the accuracy of self-evaluation, self-scores and expert-scores were compared using a Wilcoxon signed-rank test. Twenty-seven surgical trainees completed the simulation, with a mean time to completion (TTC) of 40.3 minutes (range 14.2-106.0 minutes). For the entire cohort, the median ALI self-score was 4 (range 3-10), while the median ALI expert-score was 5.5 (range 2.5-9.5). There was a significant difference between the ALI self-score and the expert-score (p<0.001). When grouped by experience level, there was no significant difference between self-score and expert-score within the specialist group, while there was a significant difference within the novice group (p=0.001). These findings suggest that specialist trainees are accurate assessors of their own microsurgical skills, but novice trainees tend to overestimate their technical skills. While novice trainees can engage in independent self-directed microsurgical training, they should seek expert feedback to ensure targeted training.