COVID-19 has created challenges across medicine, including in medical education, with deeply rooted impacts in the dermatology residency experience. Its effects are both acute and chronic, including: shifts to virtual education and conferences, skewed clinical experiences, negatively impacted wellness, and uncertainty in the future. As educators and mentors, it is important to recognize and address these issues so that we may remain transparent, adaptable, and engaged as we continue to build a better tomorrow for our resident trainees.