Background: The ever-expanding medical knowledge, longer work schedule and the work atmosphere ridden with litigations make the medical education a stressful phase. Stress in resident doctors goes unattended many a times. Residents also face difficulty in sleep owing to their heavy work and erratic routine. Insomnia is noted to be a common accompaniment of stress. In this background, the present study is aimed to estimate the prevalence of stress levels and the presence of insomnia among resident doctors and to assess the association between them along with their socio-demographic correlates. Methodology: Resident doctors working in three different hospitals attached to a medical college were approached; consenting participants were administered Sociodemographic pro forma, Perceived Stress Scale, and Bergen's Insomnia scale. Statistical analysis was done using SPSS software. Results: A total of 251 residents participated in the study, of which majority were females, Hindu, from an urban background, unmarried and used no psychoactive substance. Of all the residents 80% reported to be stressed and 62% had insomnia. Bergen's Insomnia scores had moderate correlation with Perceived stress scores (r = 0.453, P < 0.001). Female and sleep-deprived residents had higher stress. Residents in clinical branches and residents with long work hours had significant insomnia than their counterparts. On logistic regression analysis, duration of work hours and problem adjusting to the current place of residence significantly predicted insomnia. Conclusion: Most residents reported to be having stress and the stressed individuals had associated insomnia. Given the serious health effects of stress, there is a need to detect it early. Insomnia could be viewed as an early and soft indicator of underlying stress.