Background: Choosing a medical specialty can be either a daunting and confusing experience for some medical students and junior doctors or a foregone conclusion to others. The aim of this study is to evaluate factors affecting future specialty choice among medical students in Kuwait University. Methods: A self-administered questionnaire was used to collect data from medical students registered in Kuwait University during the academic year 2011/2012. Chi-square test and logistic regression were used to test the association between deciding a future specialty and students’ sociodemographic and academic factors. Results: Of the 422 students approached, 387 (91.7%) decided to participate. A total of 144 (37.2%) students made a decision regarding their choice of future medical specialty. Pediatrics, general surgery, and cardiology were the most desired specialties – 18 (12.5%), 17 (11.8%), and 16 (11.1%) students requested these specialties, respectively. Only 61 (42.4%) of those who selected a future specialty received advice regarding their choice. Looking for a good treatment outcome for patients (66; 45.8%) and a challenging specialty (58; 40.3%) were the most influencing incentives when selecting a future specialty. Students in the clinical phase of their study were 3.014 (95% CI: 1.498–6.065) more likely to report on their decision regarding a future specialty compared to students in the basic medical sciences phase (p=0.002). Conclusion : A variety of factors appeared to inspire medical students in Kuwait to choose a future medical specialty. When identified, these factors can be used by mentors of medical students and directors of residency training programs to motivate students to choose specialties that are limited in Kuwait.