We explored the prevalence of insomnia, confirm the associated psychological factors and current coping strategies among undergraduate medical during their clinical years. This cross-sectional, quantitative, descriptive study was conducted at the department of medical education, college of medicine, King Saud University (KSU), Riyadh, Saudi Arabia. The participants (n = 463) were the 3rd to 5th year, and intern medical clinical students. We collected responses about sleep, using the Insomnia Severity Index (ISI). We also used Kessler-10 (K10), Psychological Distress and the Patient Health Questionnaire (PHQ-9). Items related to Coping strategies were also used from our previously published study and COVID-19 issues were explored using a self-developed questionnaire. According to the ISI ranking, 162 (34.9 %) of the participants had insomnia, among them 57.4% of females and 42.6% were males. Age groups between 22 and 25 have more sleeping disorder (43.2%) as compared to other age groups. 3rd-year students have more insomnia 36.41% as compared to other years. Individuals with insomnia symptoms were more likely (1.67 times higher) to be female students (OR = 1.67; P = 0.005) as compared to male students. A significantly high prevalence (3.37 times high) of insomnia was noted for those students or interns who have attended their clinical training irregularly as compare to regularly attending participants (OR = 2.32; P = 0.12) during COVID-19. Transition time i.e. year 3 of medical program was more stressful for the students and female students perceived stress and insomnia more than their male counterparts. It is important to address identified disorder early in order to reduce psychological morbidity and its harmful implications for medical students and young physicians.