Objectives: This study aimed to assess patterns of coffee consumption among medical students at Al-Kindy College of Medicine, evaluate awareness of its benefits and adverse effects, and explore possible associations between caffeine intake and menstrual characteristics among female students.Methods: A descriptive cross-sectional study was conducted between November 2023 and February 2024 among 297 undergraduate medical students selected by convenience sampling. Data were collected through a validated, self-administered online questionnaire covering sociodemographic characteristics, coffee-drinking habits, perceived effects, and menstrual patterns. Descriptive and inferential analyses were performed using SPSS version 25. Associations were examined using the chi-square test, with p < 0.05 considered statistically significant. Ethical approval was obtained from the Al-Kindy College of Medicine Research Ethics Committee (Approval No. 11/2023-10-OBG-22).Results: Among the participants, 71.9% reported regular coffee consumption, with females representing 56.9% of drinkers. The majority (62.1%) consumed one to two cups daily, primarily in the morning (28.1%). The most common motivations were improving academic performance (22.1%) and enhancing concentration (17.9%). Reported side effects included palpitations (23.4%), fatigue (11.5%), anxiety (11.5%), and sleep disturbances (34.9%) (p < 0.001). Among female students, 42.2% reported no change in coffee intake during menstruation, and 43.5% indicated no effect on menstrual pain. The relationship between coffee consumption and menstrual pain was statistically significant (÷² = 19.8, p < 0.001), but had a moderate effect size (Cramer’s V = 0.32).Conclusion: Coffee consumption was highly prevalent among medical students, driven mainly by academic demands rather than cultural habits. Most students consumed caffeine in moderate amounts, although sleep disturbance and palpitations were common. No strong evidence was found linking coffee intake to menstrual pain. Educational interventions are recommended to promote awareness of safe caffeine use and its potential health effects.